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Journal articles on the topic 'Bis-adducts'

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Author: Grafiati

Published: 11 March 2023

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1

Tagliatesta, Pietro, Angelo Lembo, Valentina Orlandi, and Marzia Nuccetelli. "Synthesis and characterization of new β-disubstituted porphyrin-[60]fullerene cyclic bis-adducts." Journal of Porphyrins and Phthalocyanines 14, no. 08 (August 2010): 727–31. http://dx.doi.org/10.1142/s1088424610002537.

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Two new β-disubstituted porphyrin-[60]fullerene cyclic bis-adducts have been synthesized using a tetraphenylporphyrin bearing two rigid aldehydic branches directly linked to the same pyrrole ring. The obtained bis-adducts with [60]fullerene have been characterized by mass and NMR spectroscopy.

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2

Yusifli, F. Kh, N. A. Aliyeva, and G. A. Ramazanov. "USE OF BIS-ADDUCTS OF ETHANEDITHIOL WITH ALKYL- AND CYCLOALKYL SUBSTITUTED METHYLENE DIOXOLANES IN THE COMPOSITION OF POLYVINYL CHLORIDE." Chemical Problems 21, no. 1 (2023): 72–77. http://dx.doi.org/10.32737/2221-8688-2023-1-72-77.

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By free radical addition of ethanedithiol to alkyl- and cycloalkyl-substituted methylene dioxolanes, the bis-adducts tested then as a plasticizer for PVC have been obtained. It has been established as a result of the carried out investigations that the introduction of the synthesized compounds into PVC composition improves the physical-mechanical properties, which has been connected with the availability of sulfur atoms, carbonyl groups and ether bond in the molecules of bis-adducts. The high operational indices from PVCplastics indicate good plasticizing properties of the synthesized bis-adducts, and therefore they can be recommended for practical use.

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3

Sharma, Mousami, Anju Sharma, and Renu Sachar. "Synthesis and Characterization of the Adducts of Morpholinedithioccarbamate Complexes of Oxovanadium (IV), Nickel(II), and Copper(II) with Piperidine and Morpholine." E-Journal of Chemistry 9, no. 4 (2012): 1929–40. http://dx.doi.org/10.1155/2012/689501.

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A series of 1:1 adducts of bis(morpholinedithiocarbamato) complex of VO(IV), 1:1 and 1:2 adducts of bis(morpholinedithiocarbamato) complexes of Ni(II) and Cu(II) with piperidine and morpholine have been synthesized and characterized by elemental analysis, molar conductance, magnetic susceptibility, IR, UV-Vis, and TGA/DTA techniques. Analytical data reveals that VO(IV) complex forms only 1:1 adducts with the formula [VO(morphdtc)2L].H2O while Ni(II) and Cu(II) complexes form both 1:1 and 1:2 adducts with 1:1 adducts having general formula Ni(morphdtc)2.L and Cu(morphdtc)2.L and 1:2 adducts having general formula Ni(morphdtc)2.L2and Cu(morphdtc)2.L2(morphdtc = morpholinedithiocarbamate, L = morpholine and piperidine). Antifungal activity of some complexes has been carried out against the fungal strainFusarium oxysporium. Thermal studies indicate a continuous weight loss. A square pyramidal geometry has been proposed for the 1:1 adducts of Ni(II) and Cu(II) complexes while an octahedral geometry has been proposed for the 1:1 adducts of VO(IV) and for the 1:2 adducts of Ni(II) and Cu(II) complexes.

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4

Baer-Dubowska, W. "Alternative pathways of polycyclic aromatic hydrocarbons activation: the formation of polar DNA adducts." Acta Biochimica Polonica 46, no. 2 (June 30, 1999): 263–74. http://dx.doi.org/10.18388/abp.1999_4160.

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Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental pollutants, and some are potent carcinogens in rodents. Carcinogenic PAHs are activated in the cells to metabolites that react with DNA to form covalent adducts. For most PAHs the reactive, electrophilic species which bind to DNA, are bay-region diol-epoxides. Application of 32P-postlabeling to PAH-DNA adducts analysis revealed that for some PAHs the adduct profiles generated in model systems are more complex and include adducts which are more polar than those formed by classic bay-region diol-epoxides. This minireview summaries the information gained on typical representatives of polar PAH-DNA adducts. Formation of triol-epoxide-DNA adducts was proposed for chrysene and a non-alterant PAH, benzo[b]fluoranthene (B[b]F). 5-OH-B[b]F, the precursor of B[b]F triol-epoxide, was found to be a potent tumor initiator in mouse skin. For planar PAHs such as dibenzanthracenes the possibility of bis-diol epoxide-DNA adducts formation was suggested. The most comprehensive data were obtained for dibenz[a,j]anthracene (DB[a,j]A). This hydrocarbon when applied to SENCAR mouse skin forms up to 23 species of adducts, most of which are polar. Among these polar adducts seven were identified as derived from DB[aj]A-3,4-10,11-bis-diol. Analysis of tumor-initiating activity showed, however, that this proximate metabolite was inactive in this respect. In contrast, an excellent correlation was observed between levels of less polar DNA adducts (i.e. those derived from bay-region diolepoxides) and skin tumor initiating activity of DB[a,j]A. Thus, while triol-epoxides seems to be involved in tumor initiating activity of the parent compound, non alterant B[b]F, the significance of bis-diol epoxide-DNA adducts, at least those derived from DB[aj]A, is minor.

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5

Hossain, MM, ME Halim, MM Islam, K. Akhter, SM Ahmed, UKR Romman, and MG Ahmed. "Michael 1:1 adducts by acid catalyzed reaction during synthesis of spiro and spiroketal compounds." Bangladesh Journal of Scientific and Industrial Research 55, no. 4 (December 27, 2020): 283–88. http://dx.doi.org/10.3329/bjsir.v55i4.50967.

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Four Michael 1:1 adducts 2-[1,5-bis-(2-methoxyphenyl)-3-oxo-pent-4-enyl]-cyclohexane-1,3- dione 3a, 2-[1,5-bis-(2-methylphenyl)-3-oxo-pent-4-enyl]-cyclohexane-1,3-dione 3b, 2-[1,5-bis- (2-chlorophenyl)-3-oxo-pent-4-enyl]-cyclohexane-1, 3-dione 3c and 2-[1,5-Bis-(2-chloro- phenyl)- 3-oxo-pent-4-enyl]-5,5-dimethyl-cyclohexane-1,3-dione 3d have been synthesised by the application of Michael reaction between 1, 3-cyclohexanedione 1a or dimedone (5, 5-dimethylcy clohexane-1, 3-dione) 1b and trans,trans diarylideneacetone [1,5-diaryl-1,4-pentadien-3-one] 2a-c using acid catalyst. These adducts may be regarded as the intermediate of spiro [5.5] undecane compounds which can be achieved effectively via intramolecular cyclization of the Michael 1:1 adduct. The structures of the Michael 1:1 adducts 3a-d were determined by their UV, IR, 1H-NMR, 13C-NMR, DEPT-135 spectral data, HRMS and elemental analyses. Bangladesh J. Sci. Ind. Res.55(4), 283-288, 2020

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6

Kour, Gurpreet, Inderjeet Kour, and Renu Sachar. "Synthesis and Characterization of the Adducts of Bis(O-ethyldithiocarbonato)copper(II) with Substituted Pyridines." International Journal of Inorganic Chemistry 2013 (December 22, 2013): 1–4. http://dx.doi.org/10.1155/2013/502856.

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Monomeric five coordinated adducts of bis(O-ethyldithiocarbonato)copper(II) of general formula [Cu(C2H5OCS2)2(L)], [L = 2-, 3-, 4-methylpyridines and 2-, 3-, 4-ethylpyridines] have been synthesized and characterized by elemental analysis, i.r. and electronic spectroscopy, magnetic and conductivity measurements. Analytical results show that the adducts have 1 : 1 stoichiometry. The adducts were found to be paramagnetic and their magnetic moments at room temperature lie within the 1.81–1.94 B.M. range and this indicates the presence of one unpaired electron. All the adducts have distorted square pyramidal geometry.

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7

Bispinghoff, Mark, Aaron M. Tondreau, Hansjörg Grützmacher, Charly A. Faradji, and Paul G. Pringle. "Carbene insertion into a P–H bond: parent phosphinidene–carbene adducts from PH3 and bis(phosphinidene)mercury complexes." Dalton Transactions 45, no. 14 (2016): 5999–6003. http://dx.doi.org/10.1039/c5dt01741f.

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The insertion of an N-heterocyclic carbene into a P–H bond is the first step in a new synthesis of parent phosphinidene–carbene adducts from PH₃. These adducts are used to generate bis(phosphinidene)mercury(ii) complexes.

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8

Sedenkova, Kseniya N., Elena B. Averina, Yuri K. Grishin, Julia V. Kolodyazhnaya, Victor B. Rybakov, Tamara S. Kuznetsova, Audrey Hughes, Gabriel dos Passos Gomes, Igor V. Alabugin, and Nikolay S. Zefirov. "Substituent effects on stereoselectivity of dihalocarbene reactions with cyclohexadiene and on the reactivity of bis-dihalocyclopropanes in electrophilic nitrations en route to pyrimidine N-oxides." Organic & Biomolecular Chemistry 15, no. 44 (2017): 9433–41. http://dx.doi.org/10.1039/c7ob02463k.

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9

Wang, Guowei, Linghua Zhuang, and Jintang Wang. "A Route to a Tetrabenzothiazole from Michael Bis-Addition Compounds." Journal of Chemical Research 2009, no. 4 (April 2009): 212–13. http://dx.doi.org/10.3184/030823409x435883.

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10

Talbi, Arbia, Aïcha Arfaoui, Talia Bsaibess, Mohamed Lotfi Efrit, Anne Gaucher, Damien Prim, and Hédi M′Rabet. "Selective synthesis of mono- and bis-butenolide α-aminomethyl adducts." Organic & Biomolecular Chemistry 15, no. 15 (2017): 3298–303. http://dx.doi.org/10.1039/c7ob00206h.

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11

Schüler, Philipp, Helmar Görls, Matthias Westerhausen, and Sven Krieck. "Bis(trimethylsilyl)amide complexes of s-block metals with bidentate ether and amine ligands." Dalton Transactions 48, no. 24 (2019): 8966–75. http://dx.doi.org/10.1039/c9dt01426h.

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The synthesis of the bis(trimethylsilyl)amide complexes of alkali and alkaline-earth metals with bidentate ether and amine bases 1,2-bis(dimethylamino)ethane (tmeda), dimethyl-methoxyethylamine (dmmea), and 1,2-dimethoxyethane (dme) succeedsviaaddition of these bases to coligand-free complexes orvialigand exchange of thf adducts.

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12

Trinh, Thi Minh Nguyet, Franck Schillinger, Sebastiano Guerra, Eric Meichsner, Iwona Nierengarten, Uwe Hahn, Michel Holler, and Jean‐François Nierengarten. "Regioselective Preparation of Fullerene Bis‐adducts from Cleavable Macrocyclic Bis‐malonates." European Journal of Organic Chemistry 2021, no. 27 (June 22, 2021): 3770–86. http://dx.doi.org/10.1002/ejoc.202100571.

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13

Benelli, C., D. Gatteschi, C. Zanchini, R. J. Doedens, M. H. Dickman, and L. C. Porter. "EPR spectra of bis(nitroxyl) adducts of bis(hexafluoroacetylacetonato)manganese(II)." Inorganic Chemistry 25, no. 19 (September 1986): 3453–57. http://dx.doi.org/10.1021/ic00239a027.

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14

Müller, Christoph, Sven Krieck, Helmar Görls, and Matthias Westerhausen. "Synthesis of Lewis Base Adducts of Barium Bis[bis(trimethylsilyl)amide]." European Journal of Inorganic Chemistry 2016, no. 28 (September 1, 2016): 4637–42. http://dx.doi.org/10.1002/ejic.201600561.

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15

Borisova, Kseniya K., Eugeniya V. Nikitina, Roman A. Novikov, Victor N. Khrustalev, Pavel V. Dorovatovskii, Yan V. Zubavichus, Maxim L. Kuznetsov, Vladimir P. Zaytsev, Alexey V. Varlamov, and Fedor I. Zubkov. "Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control." Chemical Communications 54, no. 23 (2018): 2850–53. http://dx.doi.org/10.1039/c7cc09466c.

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16

Sellmann, Dieter, Marcus Hannakam, Falk Knoch, and Matthias Moll. "Übergangsmetallkomplexe mit Schwefelliganden, XCII. Oxidation von Thiolat-Amin- zu Schiffbase-Eisen(II)-Komplexen. Röntgenstrukturanalyse und Reaktivität von [Fe('N2S2')]2 (′N2S2′2- = Glyoxal-bis(2-mercaptoanil)(2 – )) / Transition Metal Complexes with Sulfur Ligands, XCII. Oxidation of Thiolate Amine to Schiff Base Iron(II) Complexes. X-Ray Structure Analysis and Reactivity of [Fe(′N2S2')]2 (′N2S2′2- = Glyoxal-bis(2-mercaptoanil)(2–))." Zeitschrift für Naturforschung B 47, no. 11 (November 1, 1992): 1545–50. http://dx.doi.org/10.1515/znb-1992-1107.

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Oxidation of [Fe(CO)2(′N2H2S2′')] (1) (′N2H2S2'2- = 1,2-ethanediamine-N,N′-bis(2-benzenethiolate)(2—)) gave insoluble [Fe(′N2S2')]2 (2) ('N2S2'2- = glyoxal-bis(2-mercaptoanil)(2—)). Dinuclear, thiolato-bridged 2 was characterized by single crystal X-ray structure analysis. It does not react with CO or H2, but yields bis or mono adducts with PR3 (R = Me, n-Bu, Cy).

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17

Yan, Xing-Xing, Chuang Niu, Shi-Qi Ye, Bo-Chen Zhao, and Guan-Wu Wang. "Electrochemically Promoted Benzylation of [60]Fullerooxazolidinone." Nanomaterials 12, no. 13 (July 1, 2022): 2281. http://dx.doi.org/10.3390/nano12132281.

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Benzylation of the electrochemically generated dianion from N-p-tolyl-[60]fullerooxazolidinone with benzyl bromide provides three products with different addition patterns. The product distribution can be dramatically altered by varying the reaction conditions. Based on spectral characterizations, these products have been assigned as mono-benzylated 1,4-adduct and bis-benzylated 1,2,3,16- and 1,4,9,25-adducts, respectively. The assigned 1,2,3,16-adduct has been further established by X-ray diffraction analysis. It is believed that the 1,4-adduct is obtained by decarboxylative benzylation of the dianionic species, while bis-benzylated 1,2,3,16- and 1,4,9,25-adducts are achieved via a rearrangement process. In addition, the electrochemical properties of these products have been studied.

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18

Umeyama, Tomokazu, Shogo Takahara, Sho Shibata, Kensho Igarashi, Tomohiro Higashino, Kenji Mishima, Koichi Yamashita, and Hiroshi Imahori. "cis-1 Isomers of tethered bismethano[70]fullerene as electron acceptors in organic photovoltaics." RSC Advances 8, no. 33 (2018): 18316–26. http://dx.doi.org/10.1039/c8ra02896f.

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19

Taylor, Laurence J., Brian A. Surgenor, Piotr Wawrzyniak, Matthew J. Ray, David B. Cordes, Alexandra M. Z. Slawin, and Petr Kilian. "Spontaneous dehydrocoupling in peri-substituted phosphine–borane adducts." Dalton Transactions 45, no. 5 (2016): 1976–86. http://dx.doi.org/10.1039/c5dt02539g.

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Borane adducts of peri-substituted bis(phosphines) eliminate hydrogen at room temperature, without the presence of catalysts. These reactions are the first examples of “spontaneous” phosphine–borane dehydrocoupling.

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20

Sølling, Theis I., and Leo Radom. "Exchange of Cl+ between Lone-Pair Donors and π-Donors: A Computational Study." European Journal of Mass Spectrometry 6, no. 2 (April 2000): 153–60. http://dx.doi.org/10.1255/ejms.335.

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The chemistry of mono-adducts ([Cl–X]+) between Cl+ and a Lewis base (X = NH3, H2O, HF, PH3, H2S or HCl) has been investigated using ab initio molecular orbital calculations at the G2 level. The reactions of such mono-adducts with additional Lewis bases (Y) are found to give [Y–Cl]+ plus X, generally without an intermediate barrier, via a bis-adduct [Y–Cl–X]+. The binding energies of the bis-adduct and the reaction energies are related to the donor properties of the Lewis bases. The reactions between the mono-adducts [Cl–X]+ and the π-donors ethylene and acetylene yield chloriranium and chlorirenium ions, respectively. These reactions proceed via complexes that resemble either the reactants or products depending on the sign of the reaction energy, the latter in turn being determined by the donor ability of the Lewis base. Results for the chlorine systems are compared with those for the corresponding phosphorus systems investigated previously.

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21

Charykov, N. A., V. A. Keskinov, and A. V. Petrov. "Adducts of Lower Fullerenes and Amino Acids: Synthesis, Identification, and Quantum-Mechanical Modeling of Their Physicochemical Properties." Russian Journal of Physical Chemistry A 95, no. 12 (December 2021): 2359–74. http://dx.doi.org/10.1134/s0036024421120049.

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Abstract Different ways of synthesizing bis-, tris-, and octakis-adducts of C60 and C70 lower fullerenes are considered, and their yield and purity are described. The adducts are identified by physicochemical means: elemental analysis, IR, electron spectroscopy, Raman spectroscopy, HPLC, mass spectrometry, and complex thermal analysis. Their physicochemical properties are modeled using computers, density functional theory, and molecular dynamics at the atomic-molecular level.

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22

Ali, Shamsher, Eric Hénon, Ritchy Leroy, and Georges Massiot. "Addition of Vindoline to p-Benzoquinone: Regiochemistry, Stereochemistry and Symmetry Considerations." Molecules 26, no. 21 (October 22, 2021): 6395. http://dx.doi.org/10.3390/molecules26216395.

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Vindoline and catharanthine are the major alkaloids of Catharanthus roseus and are extracted in large quantities to prepare the pharmaceutically important Vinca type alkaloids vincaleukoblastine, vincristine and navelbine. The higher yield of vindoline relative to catharanthine makes it an attractive substrate for developing new chemistry and adding value to the plant. In this context, we have reacted vindoline with a selection of electrophiles among which benzoquinone. Conditions were developed to optimize the synthesis of a mono-adduct, of five bis-adducts, and of tri-adducts and tetra-adducts, several of these adducts being mixtures of conformational isomers. Copper(II) was added to the reactions to promote reoxidation of the intermediate hydroquinones and simplify the reaction products. The structures were solved by spectroscopic means and by symmetry considerations. Among the bis-isomers, the 2,3-diadduct consists of three unseparable species, two major ones with an axis of symmetry, thus giving a single set of signals and existing as two different species with indistinguishable NMR spectra. The third and minor isomer has no symmetry and therefore exhibits nonequivalence in the signals of the two vindoline moieties. These isomers are designated as syn (minor) and anti (major) and there exists a high energy barrier between them making their interconversion difficult. DFT calculations on simplified model compounds demonstrate that the syn-anti interconversion is not possible at room temperature on the NMR chemical shift time scale. These molecules are not rigid and calculations showed a back-and-forth conrotatory motion of the two vindolines. This “windshield wiper” effect is responsible for the observation of exchange correlations in the NOESY spectra. The same phenomenon is observed with the higher molecular weight adducts, which are also mixtures of rotational isomers. The same lack of rotations between syn and anti isomers is responsible for the formation of four tri-adducts and of seven tetra-adducts. On a biological standpoint, the mono adduct displayed anti-inflammatory properties at the 5 μM level while the di-adducts and tri-adducts showed moderate cytotoxicity against Au565, and HeLa cancer cell lines.

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23

Soleimani, Ebrahim, Katherine N. Robertson, Cory C. Pye, and Jason A. C. Clyburne. "Homolytic cleavage of Lawesson's reagent: N-heterocyclic carbene complexes of ArPS2 (Ar = 4-CH3O-C6H4)." Dalton Transactions 47, no. 18 (2018): 6299–303. http://dx.doi.org/10.1039/c8dt00457a.

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Lawesson's reagent has been shown to react with the N-heterocyclic carbenes [1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes) and 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene (SIPr)] to give adducts of the general form NHC·P(S)₂-C₆H₄OCH₃.

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24

Erber, Luke, Samantha Goodman, Caitlin Jokipii Krueger, Ivan Rusyn, and Natalia Tretyakova. "Quantitative NanoLC/NSI+-HRMS Method for 1,3-Butadiene Induced bis-N7-guanine DNA-DNA Cross-Links in Urine." Toxics 9, no. 10 (October 2, 2021): 247. http://dx.doi.org/10.3390/toxics9100247.

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1,3-Butadiene (BD) is a common environmental and industrial chemical widely used in plastic and rubber manufacturing and also present in cigarette smoke and automobile exhaust. BD is classified as a known human carcinogen based on evidence of carcinogenicity in laboratory animals treated with BD by inhalation and epidemiological studies revealing an increased risk of leukemia and lymphohematopoietic cancers in workers occupationally exposed to BD. Upon exposure via inhalation, BD is bioactivated to several toxic epoxides including 3,4-epoxy-1-butene (EB), 3,4-epoxy-1,2-butanediol (EBD), and 1,2,3,4-diepoxybutane (DEB); these are conjugated with glutathione and excreted as 2-(N-acetyl-L-cystein-S-yl)-1-hydroxybut-3-ene/1-(N-acetyl-L-cystein-S-yl)-2-hydroxybut-3-ene (MHBMA), 4-(N-acetyl-L-cystein-S-yl)-1,2-dihydroxybutane (DHBMA), and 1,4-bis-(N-acetyl-L-cystein-S-yl)butane-2,3-diol (bis-BDMA). Exposure to DEB generates monoalkylated DNA adducts, DNA-DNA crosslinks, and DNA-protein crosslinks, which can cause base substitutions, genomic rearrangements, and large genomic deletions. In this study, we developed a quantitative nanoLC/NSI+-HRMS methodology for 1,4-bis-(gua-7-yl)-2,3-butanediol (bis-N7G-BD) adducts in urine (LOD: 0.1 fmol/mL urine, LOQ: 1.0 fmol/mL urine). This novel method was used to quantify bis-N7G-BD in urine of mice treated with 590 ± 150 ppm BD for 2 weeks (6 h/day, 5 days/week). Bis-N7G-BD was detected in urine of male and female BD-exposed mice (574.6 ± 206.0 and 571.1 ± 163.4 pg/mg of creatinine, respectively). In addition, major urinary metabolites of BD, bis-BDMA, MHBMA and DHBMA, were measured in the same samples. Urinary bis-N7G-BD adduct levels correlated with DEB-derived metabolite bis-BDMA (r = 0.80, Pearson correlation), but not with the EB-derived DNA adducts (EB-GII) or EB-derived metabolites MHBMA and DHBMA (r = 0.24, r = 0.14, r = 0.18, respectively, Pearson correlations). Urinary bis-N7G-BD could be employed as a novel non-invasive biomarker of exposure to BD and bioactivation to its most mutagenic metabolite, DEB. This method will be useful for future studies of 1,3-butadiene exposure and metabolism.

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25

Eder, Erwin, and Christian Hoffman. "Identification and characterization of deoxyguanosine-crotonaldehyde adducts. Formation of 7,8 cyclic adducts and 1,N2,7,8-bis-cyclic adducts." Chemical Research in Toxicology 5, no. 6 (November 1992): 802–8. http://dx.doi.org/10.1021/tx00030a012.

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26

Do, Thomas H., and Seth N. Brown. "Mono- and bimetallic pentacoordinate silicon complexes of a chelating bis(catecholimine) ligand." Dalton Transactions 48, no. 30 (2019): 11565–74. http://dx.doi.org/10.1039/c9dt02475a.

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27

Ðorđević, Luka, Lorenzo Casimiro, Nicola Demitri, Massimo Baroncini, Serena Silvi, Francesca Arcudi, Alberto Credi, and Maurizio Prato. "Light‐Controlled Regioselective Synthesis of Fullerene Bis‐Adducts." Angewandte Chemie International Edition 60, no. 1 (September 17, 2020): 313–20. http://dx.doi.org/10.1002/anie.202009235.

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28

Schmidbaur, Hubert, Wolfgang Bublak, Brigitte Huber, and Gerhard Müller. "Arene Adducts with Weak Interactions: Hexaethylbenzene–bis(tribromoarsane)." Angewandte Chemie International Edition in English 26, no. 3 (March 1987): 234–36. http://dx.doi.org/10.1002/anie.198702341.

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29

Ðorđević, Luka, Lorenzo Casimiro, Nicola Demitri, Massimo Baroncini, Serena Silvi, Francesca Arcudi, Alberto Credi, and Maurizio Prato. "Light‐Controlled Regioselective Synthesis of Fullerene Bis‐Adducts." Angewandte Chemie 133, no. 1 (September 17, 2020): 317–24. http://dx.doi.org/10.1002/ange.202009235.

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30

Askari, Syed, Susan Lee, Robert R. Perkins, and John R. Scheffer. "Trapping of o-quinodimethane with p-quinones: synthesis of tetrahydro-1,4-anthracenediones." Canadian Journal of Chemistry 63, no. 12 (December 1, 1985): 3526–29. http://dx.doi.org/10.1139/v85-578.

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Previous work from our laboratory has been concerned with investigating the photochemical reactivity of the tetrahydro-1,4-napthalenedione system, both in solution and the solid state. The results obtained prompted us to extend our studies to the analogous tetrahydro-1,4-anthracenedione system. The most direct method of synthesis of the desired compounds is through Diels–Alder addition of o-quinodimethane to p-quinones. Because of the ease with which the adducts would be expected to undergo bis-enolization to the corresponding hydroquinones, their preparation requires mild, neutral conditions. After much experimentation, success was achieved using the Durst–Charlton sulfur dioxide extrusion method for generating o-quinodimethane from 3,6-dihydro-1,2-oxathiin-2-oxide. Insitu trapping using p-benzoquinone and other substituted p-quinones afforded the desired adducts in reasonable yields. In the case of duroquinone and 2,3-dimethyl-1,4-naphthalenedione, fluoride ion-catalyzed generation of o-quinodimethane from [o-[α-(trimethylsilyl)methyl]benzyl]trimethylammonium bromide by the method of Ito also gave acceptable results; however, the bis-enolizable adducts were not stable under these eaction conditions.

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31

Asghar, Basim H. M., Michael R. Crampton, and Chukwuemeka Isanbor. "Carbanion reactivity — σ-adduct formation and elimination in the reactions of the carbanion from bis(phenylsulfonyl)methane with 4-nitrobenzofurazan derivatives." Canadian Journal of Chemistry 86, no. 3 (March 1, 2008): 225–29. http://dx.doi.org/10.1139/v08-010.

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1H NMR studies in [2H6]-DMSO show that the carbanion 4 from bis(phenylsulfonyl)methane reacts with 4,6-dinitrobenzofuroxan to yield a σ-adduct that undergoes base-catalysed elimination to yield an alkene derivative. Rate constants, measured spectrophotometrically, are reported for the corresponding reactions in methanol of 4 with 4-nitrobenzofurazan and some derivatives that give adducts at the 5-position. The intrinsic rate constant, ko, for this process has a value of 1.5 ± 0.5. The 5-adducts undergo methoxide-catalysed elimination of phenylsulfinic acid to yield alkene derivatives and rate constants for this process are reported.Key words: carbanions, 4-nitrobenzofurazan, σ-adducts, elimination reactions.

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32

Farquharson, Melvin J., and J. Stephen Hartman. "Bis(tertiary amine)dihaloboron cations and related species: nuclear magnetic resonance and fast atom bombardment mass spectrometry studies." Canadian Journal of Chemistry 67, no. 11 (November 1, 1989): 1711–23. http://dx.doi.org/10.1139/v89-264.

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The formation of four-coordinate haloboron cations from aliphatic tertiary amine adducts of the mixed boron trihalides by heavy halogen displacement has been systematically studied by 19F and 11B nuclear magnetic resonance and positive ion fast atom bombardment mass spectrometry (FAB). Low-steric-hindrance donor molecules readily displace bromide ion from tertiary amine – bromodifluoroborane adducts, D•BF2Br, to form difluoroboron cations D2BF2+ and DD′BF2+, but the corresponding dibromofiuoroborane and tribromoborane adducts are highly resistant to bromide ion displacement. Bis(tertiary amine)dichloroboron and -chloroiodoboron cations can be obtained by selective iodide displacement from D•BCl2I and D•BClI2. Fast atom bombardment mass spectrometry selectively detects the haloboron cations in preference to the neutral adducts in mixtures, and is a valuable complement to nmr in monitoring formation of the haloboron cations as well as any ionic by-products. Keywords: difluoroboron cations, dihaloboron cations, NMR, 11B, 19F, fast atom bombardment (FAB), ligand substitution, redistribution reactions.

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33

Dent, BR, B. Halton, and AMF Smith. "Synthesis and Trapping of Some Reactive Cyclopropenes." Australian Journal of Chemistry 39, no. 10 (1986): 1621. http://dx.doi.org/10.1071/ch9861621.

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Commencing with 1,1,2-tribromo-2-trimethylsilylcyclopropane (1d), 1,2- dibromo -and 1-bromo-2-trimethylsilyl-cyclopropene (2d) and (6) are easily prepared. These reactive cyclopropenes decompose on standing at ambient temperature but can be trapped in situ as Diels-Alder adducts (4) and (5). Furthermore, 1,2-bis( trimethylsilyl )- and 1- trimethylsilyl-cyclopropene (8) and (9) can be prepared from cyclopropane (1d) via the bromo - and lithio-trimethylsilylcyclopropenes (6) and (7) in a 'one-pot' procedure and trapped as adducts (4e,f) respectively.

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34

Schumann, Herbert, Mario Glanz, Jochen Gottfriedsen, Sebastian Dechert, and Dietmar Wolff. "Lewis-acidic organometallic compounds of the lanthanides and the alkaline earth metals as catalysts for the activation of carbonyl groups." Pure and Applied Chemistry 73, no. 2 (January 1, 2001): 279–82. http://dx.doi.org/10.1351/pac200173020279.

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1,3-dialkyl-4,5-dimethylimidazol-2-ylidenes form adducts with various bis (alkylcyclopentadienyl) complexes of magnesium, calcium, strontium, barium, samarium, and ytterbium. The X-ray structures of selected metallocenes and carbene adducts are discussed. Liquid-crystalline homo- and block copolymers with a narrow molecular mass distribution index were obtained in high yields by living polymerization of mesogenic methacrylates with organosamarium complexes. Depending on the structure of the catalyst and the polarity of the solvent used, different, partially competitive reaction mechanisms are observed.

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35

Kohyama, Aki, Michihiro Fukuda, Shunsuke Sugiyama, Hiroyuki Yamakoshi, Naoki Kanoh, Chikashi Ishioka, Hiroyuki Shibata, and Yoshiharu Iwabuchi. "Reversibility of the thia-Michael reaction of cytotoxic C5-curcuminoid and structure–activity relationship of bis-thiol-adducts thereof." Organic & Biomolecular Chemistry 14, no. 45 (2016): 10683–87. http://dx.doi.org/10.1039/c6ob01771a.

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A panel of GO-Y030-bis-thiol-adducts were synthesized and the structure–reactivity relationship regarding the retro thia-Michael reaction as well as the cell growth inhibitory activity against human colon cancer HCT116 were evaluated.

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36

Jones, Peter G., Jerzy Ossowski, Piotr Kus, and Ina Dix. "Three Crystal Structures of Terephthalic Acid Salts of Simple Amines." Zeitschrift für Naturforschung B 64, no. 7 (July 1, 2009): 865–70. http://dx.doi.org/10.1515/znb-2009-0716.

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Diphenethylamine forms two adducts (1 : 1, 1a and 2 : 1, 1b) with terephthalic acid (H2TPA). The former is bis(diphenethylammonium)H2TPA・TPA2− and the latter is bis(diphenethylammonium) ・TPA2−. The amine cis-2,6-dimethylpiperidine forms a hydrated 2 : 1 adduct, bis(2,6-dimethylpiperidinium) ・TPA2−・H2O (2). The crystal structures of all three compounds were determined. All H2TPA and TPA2− residues display inversion symmetry, while the water oxygen atom of 2 lies on a twofold axis. Packing analyses have identified some supramolecular synthons known from related structures.

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37

Merlino, Antonello, Cinzia Verde, Guido di Prisco, Lelio Mazzarella, and Alessandro Vergara. "Reduction of ferric hemoglobin fromTrematomus bernacchiiin a partial bis-histidyl state produces a deoxy coordination even when encapsulated into the crystal phase." Spectroscopy 22, no. 2-3 (2008): 143–52. http://dx.doi.org/10.1155/2008/328463.

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Crystallographic and spectroscopic evidences on Antarctic fish hemoglobins (AFHbs) have revealed that their ferric tetramers at physiological pH are in a mixed |α(aquo-met)/β(bis-histidyl) coordination state and show a quaternary structure intermediate between the classical R and T states (H state). Ferric bis-histidyl adducts (hemichromes) have been also observed in some mammalian Hbs. In order to clarify whether hemichrome in AFHbs can be converted into a ferrous bis-histidyl adduct (hemochrome), at least in the crystal phase, chemical reduction of ferric hemoglobins fromTrematomus bernacchii(HbTb) single crystals has been followed via Raman microscopy. The results of this analysis reveal that in HbTb, upon reduction, the bis-histidyl coordination is disrupted in favor of a penta-coordinated ferrous deoxy state, with no evidence of hemochrome. These data are in agreement with UV/Vis absorption spectra in solution. Furthermore, our data are also indirectly supported by the observation that upon reduction with dithionite, the ferric HbTb crystals crack and lose their diffraction power: in the crystalline state, the quaternary structure transition from the H to the T state is not compatible with the crystal packing. Altogether these data indicate that if bis-histidyl adducts have a functional significance in AFHbs, this function refers to a stable ferric state, or to a transient, though never detected, ferrous species.

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38

Datta, R. N., A. H. M. Schotman, A. J. M. Weber, F. G. H. van Wijk, P. J. C. van Haeren, J. W. Hofstraat, A. G. Talma, and A. G. V. D. Bovenkamp-Bouwman. "Biscitraconimides as Anti-Reversion Agents for Diene Rubbers: Spectroscopic Studies on Citraconimide-Squalene Adducts." Rubber Chemistry and Technology 70, no. 1 (March 1, 1997): 129–45. http://dx.doi.org/10.5254/1.3538413.

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Abstract The mechanism of anti-reversion activity of biscitraconimides (BCI) during rubber vulcanization has been investigated. Biscitraconimides form crosslinks by reaction with chain modifications which are formed during the reversion process. These additional crosslinks compensate for the sulfidic crosslinks that are lost during the reversion. To allow structural assignments of the adducts formed between rubber and citraconimides, squalene has been used as a simple model system in combination with the currently used additives and sulphur. The products were identified as Diels—Alder adducts of conjugated polyenes, formed during reversion, with citraconimide. The nuclear magnetic resonance (NMR) spectroscopic assignments of the products are discussed. Furthermore the quantification of squalene-BCI adducts via NMR and mass spectrometry (MS) using 13C labelled 1,3-bis (citraconimidomethyl) benzene (BCI-MX) is described. It was found that under the applied conditions (2 h, 170 °C), approximately 80% of the citraconimide groups are converted into squalene-BCI adducts. Diels—Alder adducts are the main reaction products of the reaction. Products from an ene reaction are formed as minor component (less than 20%).

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39

Dickie, Diane A., Raymond P. Ulibarri-Sanchez, and Richard A. Kemp. "Zwitterionic CS2 Adducts of Bis(dialkylphosphino)amines: Syntheses, Spectroscopy, and Structures." Australian Journal of Chemistry 68, no. 3 (2015): 351. http://dx.doi.org/10.1071/ch14535.

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Both bis(diisopropylphosphino)amine and bis(di-t-butylphosphino)amine react with CS2 to give bright red zwitterionic adducts of the form R2P(CS2)NP(R2)H (R = iPr or tBu). The P–H tautomer is the exclusive species present in solution, and there is no evidence of CS2 lability. The tautomeric hydrogen can undergo exchange with deuterium in protic solvents such as CD3OD. The products were characterized by single-crystal X-ray diffraction, IR and multinuclear (1H, 2H, 13C, 31P) NMR spectroscopies.

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40

Dickman, Michael H., Leigh C. Porter, and Robert J. Doedens. "Bis(nitroxyl) adducts of bis(hexafluoroacetylacetonato)manganese(II). Preparation, structures, and magnetic properties." Inorganic Chemistry 25, no. 15 (July 1986): 2595–99. http://dx.doi.org/10.1021/ic00235a022.

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41

Ruiz, David A., Mohand Melaimi, and Guy Bertrand. "An efficient synthetic route to stable bis(carbene)borylenes [(L1)(L2)BH]." Chem. Commun. 50, no. 58 (2014): 7837–39. http://dx.doi.org/10.1039/c4cc03497j.

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Two unsymmetrically substituted bis(carbene)borylene adducts [(L₁)(L₂)BH] and a radical cation [(L₁)(L₂)BH˙⁺, X⁻] are prepared by two- and one-electron reduction, respectively.

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42

Sigl, Marcus, Annette Schier, and Hubert Schmidbaur. "Indium Triiodide Complexes of Bis(diphenyIphosphino)ethane (dppe) and its Disulfide (dppeS2)." Zeitschrift für Naturforschung B 54, no. 1 (January 1, 1999): 21–25. http://dx.doi.org/10.1515/znb-1999-0107.

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Bis(diphenylphosphino)ethane (dppe) and its disulfide (dppeS2) react with two equivalents of indium triiodide to give high yields of the corresponding 1:2 adducts. According to crystal structure determinations, both compounds are molecular bis-terminal complexes with the ligands in an all-trans conformation. Contrary to previous findings for complexes of the indium trihalides and of GaBr3 and Gal3 with ditertiary phosphines in fixed cis-structure [bis(diphenylphosphino)ethene or -benzene], no iodide redistribution is observed to give the ionic species [(dppe)Inl2]+ [InI4 ]- . The molecular structures are also retained in solution.

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43

Pal, Rammohan, Arpita Das Gupta, and Asok K. Mallik. "Facile Iodine-Catalyzed Michael Addition of Indoles to α,α′-Bis(arylmethylene)cyclopentanones: An Efficient Synthesis of E-2-(3-Indolylphenylmethyl)-5-phenylmethylenecyclopentanones." ISRN Organic Chemistry 2012 (November 28, 2012): 1–6. http://dx.doi.org/10.5402/2012/674629.

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Iodine-catalyzed reaction of indoles with α,α′-bis(arylmethylene)cyclopentanones afforded one diastereomer of the corresponding Michael adducts, namely, E-2-(3-indolylphenylmethyl)-5-phenylmethylenecyclopentanones, in a good yield. The products form a new group of indole derivatives.

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44

Tiu, Elisha G. V., Korinne Liosi, Safwan Aroua, and Yoko Yamakoshi. "Micelle vs. vesicle formation controlled by distal functionalization of C60–PEG conjugates." Journal of Materials Chemistry B 5, no. 32 (2017): 6676–80. http://dx.doi.org/10.1039/c7tb00829e.

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An amphiphilic C₆₀–PEG conjugate was modified by the addition of cationic moieties in the hydrophobic C₆₀ part to provide the related bis- and tris-adducts and their self-assembling structures were compared.

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45

Cameron, Donald W., Raymond L. Evans, Geoffrey I. Feutrill, Vincent A. Patrick, Brian W. Skelton, and Allan H. White. "Stereochemistry and Crystal Structures of Bis Cycloadducts of Danishefsky's Diene (Me3SiOC(=CH2)CH=CHOMe) with 2,5- and 2,6-Dichlorobenzoquinone." Australian Journal of Chemistry 56, no. 12 (2003): 1215. http://dx.doi.org/10.1071/ch03150.

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Syntheses and single crystal X-ray structural characterizations are reported for bis adducts (6) and (7) formed between Danishefsky's diene (8) with (respectively) the dienophiles 2,6- and 2,5-dichlorobenzoquinone. Formation of each adduct involves diastereocontrolled creation of six stereogenic centres.

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46

Villarejo, A. L. Doadrio, C. V. Ragel, and G. Pérez Cuevas. "bis (Xylenedithiocarboxylate)oxovanadium(IV) and Adducts with Organic Bases." Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry 22, no. 5 (May 1992): 599–614. http://dx.doi.org/10.1080/15533179208020232.

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47

Martin, Eddy, William Clegg, Ross W. Harrington, David L. Hughes, Michael B. Hursthouse, Louise Male, and Simon J. Lancaster. "Pyridine and benzonitrile adducts of bis(4-nonafluorobiphenyl)zinc." Polyhedron 29, no. 1 (January 2010): 405–13. http://dx.doi.org/10.1016/j.poly.2009.06.018.

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48

Yoshida, Kazuhiro, Shuichi Osawa, Kenji Monde, Masataka Watanabe, and Nobuyuki Harada. "Absolute Stereochemistry of Chiral C 60 Fullerene Bis-Adducts." Enantiomer: A Journal of Sterochemistry 7, no. 1 (January 2002): 23–32. http://dx.doi.org/10.1080/10242430210704.

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49

Milic, Dragana, and Maurizio Prato. "Fullerene Unsymmetrical Bis-Adducts as Models for Novel Peptidomimetics." European Journal of Organic Chemistry 2010, no. 3 (January 2010): 476–83. http://dx.doi.org/10.1002/ejoc.200900791.

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50

Hubrich, Christopher, Axel Schulz, and Alexander Villinger. "Adducts of Gallium Trichloride and Bis(trimethylsilyl)sulfur Diimide." Zeitschrift für anorganische und allgemeine Chemie 633, no. 13-14 (October 2007): 2362–66. http://dx.doi.org/10.1002/zaac.200700245.

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