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Статті в журналах з теми "Alkenes and Dienes"

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Автор: Grafiati

Опубліковано: 6 вересня 2023

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1

Dobrovolná, Zuzana, and Libor Červený. "Competitive Hydrogenation of Unsaturated Hydrocarbons by Hydrogen Transfer from Ammonium Formateon a Palladium Catalyst." Collection of Czechoslovak Chemical Communications 62, no. 9 (1997): 1497–502. http://dx.doi.org/10.1135/cccc19971497.

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Анотація:

Competitive hydrogenation of alkenes (cyclohexene, hex-1-ene, hept-1-ene, oct-1-ene) and dienes (octa-1,7-diene, cyclohexa-1,3-diene) was carried out by catalytic hydrogen transfer from ammonium formate on palladium in methanol. The adsorptivity and reactivity of the hydrocarbons decreased in the series: cyclic diene > linear diene > linear 1-alkene > cyclic alkene.

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2

Madden, Katrina S., Sylvain David, Jonathan P. Knowles, and Andrew Whiting. "Heck–Mizoroki coupling of vinyliodide and applications in the synthesis of dienes and trienes." Chemical Communications 51, no. 57 (2015): 11409–12. http://dx.doi.org/10.1039/c5cc03273c.

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Vinyliodide reacts chemoselectively under Heck–Mizoroki conditions with terminal alkenes to give diene products, including vinyl boronate esters, and the resulting dienylboronate undergoes Suzuki–Miyaura coupling with aryl, heteroaryl and alkenyl halides to access dienes and trienes.

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3

Mantrand, Nathalie, and Philippe Renaud. "Azidosulfonylation of alkenes, dienes, and enynes." Tetrahedron 64, no. 52 (December 2008): 11860–64. http://dx.doi.org/10.1016/j.tet.2008.09.096.

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4

Tsuno, Takashi. "ChemInform Abstract: Alkenes, Alkynes, Dienes, Polyenes." ChemInform 42, no. 38 (August 25, 2011): no. http://dx.doi.org/10.1002/chin.201138251.

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5

Hussein, Aqeel A. "Ru-catalysed oxidative cyclisation of 1,5-dienes: an unprecedented role for the co-oxidant." RSC Advances 10, no. 26 (2020): 15228–38. http://dx.doi.org/10.1039/d0ra02303e.

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Анотація:

The Ru-mediated oxidative cyclisation of 1,5-dienes to THF-diols proceeds with the intermediacy of NaIO₄-complexed Ru(vi) species and offers new insights into the Ru-catalysed functionalizations of alkenes and 1,5-dienes.

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6

Gong, Liu-Zhu, Pu-Sheng Wang, and Meng-Lan Shen. "Transition-Metal-Catalyzed Asymmetric Allylation of Carbonyl Compounds with Unsaturated Hydrocarbons." Synthesis 50, no. 05 (December 21, 2017): 956–67. http://dx.doi.org/10.1055/s-0036-1590986.

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Анотація:

The asymmetric allylation of carbonyl compounds is an important process for the formation of carbon–carbon bonds, generating optically active homoallylic alcohols that are versatile building blocks with widespread applications in organic synthesis. The use of readily available unsaturated hydrocarbons as allylating reagents in the transition-metal-catalyzed asymmetric allylation has received increasing interest as either a step- or an atom-economy alternative. This review summarizes transition-metal-catalyzed enantioselective allylations on the basis of the ‘indirect’ and ‘direct’ use of simple unsaturated hydrocarbons (include dienes, allenes, alkynes, and alkenes) as allylating reagents, with emphasis on highlighting conceptually novel reactions.1 Introduction2 ‘Indirect’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds2.1 Enantioselective Allylation with 1,3-Dienes2.2 Enantioselective Allylation with Allenes2.3 Enantioselective Allylation with Alkenes3 ‘Direct’ Use of Unsaturated Hydrocarbons in Asymmetric Allylation of Carbonyl Compounds3.1 Enantioselective Allylation with 1,3-Dienes3.2 Enantioselective Allylation with Allenes3.3 Enantioselective Allylation with Alkynes3.4 Enantioselective Allylation with Alkenes4 Conclusions

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7

Welker, Mark E. "Boron and Silicon-Substituted 1,3-Dienes and Dienophiles and Their Use in Diels-Alder Reactions." Molecules 25, no. 16 (August 16, 2020): 3740. http://dx.doi.org/10.3390/molecules25163740.

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Анотація:

Boron and silicon-substituted 1,3-dienes and boron and silicon-substituted alkenes and alkynes have been known for years and the last 10 years have seen a number of new reports of their preparation and use in Diels-Alder reactions. This review first covers boron-substituted dienes and dienophiles and then moves on to discuss silicon-substituted dienes and dienophiles.

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8

González-Rodríguez, Carlos, and Michael C. Willis. "Rhodium-catalyzed enantioselective intermolecular hydroacylation reactions." Pure and Applied Chemistry 83, no. 3 (January 31, 2011): 577–85. http://dx.doi.org/10.1351/pac-con-10-09-23.

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Анотація:

Rhodium-catalyzed enantioselective hydroacylation reactions allow rapid access to chiral substituted ketones. However, due to the low reactivity of disubstituted alkenes in intermolecular versions of this process, only a small number of asymmetric intermolecular reactions have been described. Strategies employed to avoid reactivity issues include the use of norbornadienes, linear dienes, acrylamides, and allenes as the alkene components. In addition, our laboratory has recently reported the rhodium-catalyzed enantioselective inter-molecular alkyne hydroacylation reaction, leading to the formation of enone products via a kinetic resolution procedure.

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9

Trifonov, A. A., I. V. Basalov, and A. A. Kissel. "Use of organolanthanides in the catalytic intermolecular hydrophosphination and hydroamination of multiple C–C bonds." Dalton Transactions 45, no. 48 (2016): 19172–93. http://dx.doi.org/10.1039/c6dt03913h.

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10

Maeda, Hajime, Hiroshi Takayama, and Masahito Segi. "Photoinduced three-component coupling reactions of electron deficient alkenes, dienes and active methylene compounds." Photochemical & Photobiological Sciences 17, no. 8 (2018): 1118–26. http://dx.doi.org/10.1039/c8pp00239h.

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11

Stevenson, Susan M., Robert F. Higgins, Matthew P. Shores, and Eric M. Ferreira. "Chromium photocatalysis: accessing structural complements to Diels–Alder adducts with electron-deficient dienophiles." Chemical Science 8, no. 1 (2017): 654–60. http://dx.doi.org/10.1039/c6sc03303b.

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12

Wang, Yuanhao, Yuanhe Li, Yijun Fan, Zhiguo Wang, and Yefeng Tang. "Palladium-catalyzed denitrogenative functionalizations of benzotriazoles with alkenes and 1,3-dienes." Chem. Commun. 53, no. 87 (2017): 11873–76. http://dx.doi.org/10.1039/c7cc07543j.

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Анотація:

Pd-Catalyzed denitrogenative functionalizations of benzotriazoles with alkenes and 1,3-dienes have been developed, which enable the rapid access of diverse ortho-amino styrenes and 2-vinylindolines, respectively.

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13

Hussain, Nazar, Madhu Babu Tatina, and Debaraj Mukherjee. "Cross dehydrogenative coupling of sugar enol ethers with terminal alkenes in the synthesis of pseudo-disaccharides, chiral oxadecalins and a conjugated triene." Organic & Biomolecular Chemistry 16, no. 15 (2018): 2666–77. http://dx.doi.org/10.1039/c8ob00168e.

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14

Sun, Wei, Ming-Peng Li, Lu-Jie Li, Qiang Huang, Meng-Yang Hu, and Shou-Fei Zhu. "Phenanthroline-imine ligands for iron-catalyzed alkene hydrosilylation." Chemical Science 13, no. 9 (2022): 2721–28. http://dx.doi.org/10.1039/d1sc06727c.

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Анотація:

Newly developed iron complexes bearing 2-imino-9-aryl-1,10-phenanthroline ligands were successfully used to catalyze hydrosilylation of terminal alkenes and conjugated dienes in high yields with excellent anti-Markovnikov selectivity.

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15

Nii, Shinsuke, Jun Terao, and Nobuaki Kambe. "Titanocene-Catalyzed Regioselective Carbomagnesation of Alkenes and Dienes." Journal of Organic Chemistry 69, no. 2 (January 2004): 573–76. http://dx.doi.org/10.1021/jo0354241.

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16

Lewis, Frederick D., Peter Teng, and Eric Weitz. "Infrared multiphoton isomerization reactions of alkenes and dienes." Journal of the American Chemical Society 108, no. 11 (May 1986): 2818–26. http://dx.doi.org/10.1021/ja00271a006.

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17

Chambers, R. D., T. Nakamura, S. J. Mullins, and F. G. Drakesmith. "Reactions of some novel perfluorinated-alkenes and dienes." Journal of Fluorine Chemistry 54, no. 1-3 (September 1991): 63. http://dx.doi.org/10.1016/s0022-1139(00)83573-3.

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18

Giner, Xavier, Carmen Nájera, Gábor Kovács, Agustí Lledós, and Gregori Ujaque. "GoldversusSilver-Catalyzed Intermolecular Hydroaminations of Alkenes and Dienes." Advanced Synthesis & Catalysis 353, no. 18 (December 2011): 3451–66. http://dx.doi.org/10.1002/adsc.201100478.

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19

Chatzoudis, Apostolos, Vasileios Giannopoulos, Frank Hollmann, and Ioulia Smonou. "Surface-Doped Graphitic Carbon Nitride Catalyzed Photooxidation of Olefins and Dienes: Chemical Evidence for Electron Transfer and Singlet Oxygen Mechanisms." Catalysts 9, no. 8 (July 27, 2019): 639. http://dx.doi.org/10.3390/catal9080639.

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Анотація:

A new photocatalytic reactivity of carbon-nanodot-doped graphitic carbon nitride (CD-C3N4) with alkenes and dienes, has been disclosed. We have shown that CD-C3N4 photosensitizes the oxidation of unsaturated substrates in a variety of solvents according to two competing mechanisms: the energy transfer via singlet oxygen (1O2) and/or the electron transfer via superoxide (O·−2). The singlet oxygen, derived by the CD-C3N4 photosensitized process, reacts with alkenes to form allylic hydroperoxides (ene products) whereas with dienes, endoperoxides. When the electron transfer mechanism operates, cleavage products are formed, derived from the corresponding dioxetanes. Which of the two mechanisms will prevail depends on solvent polarity and the particular substrate. The photocatalyst remains stable under the photooxidation conditions, unlike the most conventional photosensitizers, while the heterogeneous nature of CD-C3N4 overcomes usual solubility problems.

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20

Kippo, Takashi, and Ilhyong Ryu. "A bromine-radical mediated three-component reaction comprising allenes, electron-deficient alkenes and allyl bromides: facile synthesis of 2-bromo-1,7-dienes." Chem. Commun. 50, no. 45 (2014): 5993–96. http://dx.doi.org/10.1039/c4cc01597e.

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Анотація:

A bromine-radical mediated three-component coupling reaction was effectively achieved by the use of allenes, electron-deficient alkenes, and allyl bromides and led to the synthesis of 2-bromo-1,7-dienes in good to high yields.

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21

Li, Linjie, Yang Chu, Lu Gao, and Zhenlei Song. "Geminal bis(silane)-controlled regio- and stereoselective oxidative Heck reaction of enol ethers with terminal alkenes to give push–pull 1,3-dienes." Chemical Communications 51, no. 85 (2015): 15546–49. http://dx.doi.org/10.1039/c5cc06448a.

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Анотація:

A geminal bis(silane)-controlled regio- and stereoselective oxidative Heck reaction of enol ethers with terminal alkenes has been developed. The reaction proceeds with α,β-coupling regioselectivity to give push–pull Z,E-1,3-dienes in good yields.

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22

Dörfler, Jaika, Till Preuß, Christian Brahms, Dennis Scheuer, and Sven Doye. "Intermolecular hydroaminoalkylation of alkenes and dienes using a titanium mono(formamidinate) catalyst." Dalton Transactions 44, no. 27 (2015): 12149–68. http://dx.doi.org/10.1039/c4dt03916e.

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23

Friedman, Rebecca Keller, Kevin M. Oberg, Derek M. Dalton, and Tomislav Rovis. "Phosphoramidite-rhodium complexes as catalysts for the asymmetric [2 + 2 + 2] cycloaddition of alkenyl isocyanates and alkynes." Pure and Applied Chemistry 82, no. 7 (May 21, 2010): 1353–64. http://dx.doi.org/10.1351/pac-con-09-12-09.

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Анотація:

The discovery and development of the asymmetric rhodium-catalyzed [2 + 2 + 2] cycloaddition of alkenyl isocyanates and exogenous alkynes to form indolizinone and quinolizinone scaffolds is described. This methodology has been expanded to include substituted alkenes and dienes, a variety of sterically and electronically diverse alkynes, and carbodiimides in place of the isocyanate. Through X-ray analysis of Rh(cod)/phosphoramidite complexes additives that modify the enantio-determining step, and other experimental data, a mechanism has been proposed that explains lactam, vinylogous amide, and pyridone products and the factors governing their formation. Finally, we have applied this methodology to the synthesis of (+)-lasubine II and (–)-209D.

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24

Shainyan, Bagrat A., Mikhail Yu Moskalik, Vera V. Astakhova, Irina V. Sterkhova, and Igor A. Ushakov. "Oxidative addition of trifluoroacetamide to alkenes, 2,5-dimethylhexa-2,4-diene and conjugated cyclic dienes." Tetrahedron 71, no. 45 (November 2015): 8669–75. http://dx.doi.org/10.1016/j.tet.2015.09.001.

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25

Zard, Samir. "Sulfur Betaines from S-Propargyl Xanthates. Unusual Chemistry from a Simple Functional Group." Synthesis 51, no. 05 (January 8, 2019): 1006–20. http://dx.doi.org/10.1055/s-0037-1611638.

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Анотація:

S-Propargyl xanthates undergo upon heating a [3,3] sigmatropic rearrangement followed by a reversible ring closure into a novel betaine. This betaine can be implicated in carbon–carbon bond forming processes, in the synthesis of esters, in the inversion of secondary alcohols, in the formation of alkenes, for the generation of rigid, cisoid dienes that are highly reactive in both inter- and intra-molecular Diels–Alder cycloadditions, and in various other synthetically useful transformations.1 Introduction2 An Unexpected Transformation3 Evidence for the Betaine Intermediate4 A Method for the Synthesis of Esters and for the Inversion of Secondary Alcohols5 A General Alkylation Process6 The Case of Carbon Acids7 A Synthesis of Alkenes8 Further Trapping Experiments. Concerted or Not Concerted?9 Rigid Cisoid Dienes10 Propargyl Radicals11 Concluding Remarks

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26

Arnold, Donald R., Kimberly A. McManus, and Mary S. W. Chan. "Photochemical nucleophile–olefin combination, aromatic substitution (photo-NOCAS) reaction, Part 13. The scope and limitations of the reaction with cyanide anion as the nucleophile." Canadian Journal of Chemistry 75, no. 8 (August 1, 1997): 1055–75. http://dx.doi.org/10.1139/v97-126.

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Анотація:

The scope of the photochemical nucleophile–olefin combination, aromatic substitution (photo-NOCAS) reaction has been extended to include cyanide anion as the nucleophile. Highest yields of adducts were obtained when the alkene or diene has an oxidation potential less than ca. 1.5 V (SCE). No adducts were obtained from 2-methylpropene (9), oxidation potential 2.6 V. Oxidation of cyanide anion, by the radical cation of the alkene or diene, can compete with the combination. With the alkenes, 2,3-dimethyl-2-butene (2) and 2-methyl-2-butene (10), both nitriles and isonitriles were obtained; isonitriles were not detected from the reactions involving the dienes, 2-methyl-1,3-butadiene (11), 2,3-dimethyl-1,3-butadiene (12), 4-methyl-1,3-pentadiene (13), 2,4-dimethyl-1,3-pentadiene (14), and 2,5-dimethyl-2,4-hexadiene (6). The specificity, nitrile versus isonitrile, is explained in terms of the Hard-Soft-Acid-Base (HSAB) principle. The photo-NOCAS reaction also occurs with the allene, 2,4-dimethyl-2,3-pentadiene (15), cyanide combining at the central carbon. Factors influencing the regiochemistry of the combination step, Markovnikov versus anti-Markovnikov, have been defined. Cyanide anion adds preferentially to the less alkyl-substituted, less sterically hindered, end of an unsymmetric alkene or conjugated diene radical cation, forming the more heavily alkyl-substituted radical intermediate. High-level abinitio molecular orbital calculations (MP2/6-31G*//HF/6-31G*) have been used to determine the effect of alkyl substitution on the stability of the intermediates, β-cyano and β-isocyano alkyl radicals, and products, alkyl cyanides and isocyanides. The more heavily alkyl-substituted radical is not necessarily the more stable. The product ratio (Markovnikov versus anti-Markovnikov) must be kinetically controlled. Keywords: photochemistry, radical ions, electron transfer, nitriles, isonitriles.

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27

Grela, Karol, and Cezary Samojlowicz. "Olefin metathesis reactions of sulfur containing alkenes and dienes." Arkivoc 2011, no. 4 (January 17, 2011): 71–81. http://dx.doi.org/10.3998/ark.5550190.0012.407.

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28

Nájera, Carmen, and Xavier Giner. "Silver-Catalyzed Intermolecular Hydroamination of Alkenes and 1,3-Dienes." Synlett 2009, no. 19 (October 15, 2009): 3211–13. http://dx.doi.org/10.1055/s-0029-1218297.

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29

Chang, Susan L. P., and David I. Schuster. "Fluorescence quenching of 9,10-dicyanoanthracene by dienes and alkenes." Journal of Physical Chemistry 91, no. 13 (June 1987): 3644–49. http://dx.doi.org/10.1021/j100297a036.

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30

Kubo, Yasuo, Kazuyuki Kiuchi, and Isamu Inamura. "Photochemical Reactions of 1,2-Dicyanonaphthalene with Alkenes and Dienes." Bulletin of the Chemical Society of Japan 72, no. 5 (May 1999): 1101–8. http://dx.doi.org/10.1246/bcsj.72.1101.

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31

Pavlova, Z. F., E. S. Lipina, and V. V. Perekalin. "Conjugated 1,2- and 1,4-Nitrothio(sulfonyl)alkenes and -Dienes." Sulfur reports 16, no. 2 (April 1995): 149–70. http://dx.doi.org/10.1080/01961779508048737.

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32

Britten, Thomas K., Mark G. McLaughlin, Ashley J. Basson, and Dean D. Roberts. "Aza-Peterson Olefinations: Rapid Synthesis of (E)-Alkenes." Synthesis 53, no. 19 (April 28, 2021): 3535–44. http://dx.doi.org/10.1055/a-1493-6670.

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Анотація:

AbstractAn aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser’s base and added to N-phenyl imines or ketones to directly give the desired products in high yields.

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33

Hanson, James R., and Ismail Kiran. "The Oxidation of Some Steroidal Dienes and Trienes with Chromic Acid." Journal of Chemical Research 23, no. 10 (October 1999): 594–95. http://dx.doi.org/10.1177/174751989902301004.

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Анотація:

The chromic acid oxidation of steroidal 2,4- and 3,5-dienes and 2,4,6-trienes is shown to take place at the secondary termini of the alkenes rather than at the allylic positions and is rationalized in terms of a sequence of 1:4-additions of chromic acid.

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34

Ding, Ran, Liang Li, Ya-Ting Yu, Bing Zhang, and Pei-Long Wang. "Photoredox-Catalyzed Synthesis of 3-Sulfonylated Pyrrolin-2-ones via a Regioselective Tandem Sulfonylation Cyclization of 1,5-Dienes." Molecules 28, no. 14 (July 17, 2023): 5473. http://dx.doi.org/10.3390/molecules28145473.

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Анотація:

A mild, visible-light-induced, regioselective cascade sulfonylation-cyclization of 1,5-dienes with sulfonyl chlorides through the intermolecular radical addition/cyclization of alkenes C(sp2)-H was developed. This procedure proceeds well and affords a mild and efficient route to a range of monosulfonylated pyrrolin-2-ones at room temperatures.

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35

Vicera, Clara, Raphael Dada, and Rylan J. Lundgren. "Z-Selective Hydrofunctionalization of Dienes." Alberta Academic Review 2, no. 2 (September 23, 2019): 77–78. http://dx.doi.org/10.29173/aar74.

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Анотація:

Olefins play a fundamental role in synthetic organic chemistry because they are useful building blocks that create molecules. However, geometry control (E- vs Z-) in olefin synthesis is of utmost importance because the olefin geometry has a tremendous impact on its physical, chemical and biological properties. Additionally, Z-olefins are less stable compared to their E-olefin counterparts; due to this difference, general methods to make olefins results in more cases of E-olefins production with relatively fewer Z-olefins caused by its instability. It has been reported that Z-olefins can be synthesized from dienes through a rhodium-catalyzed formate mediated transformation, with tolerance to several reducible functional groups. With this successful method in hand, the focus is to make functionalized Z-alkenes while still maintaining tolerance to reducible functional groups under mild reaction conditions. Thus, this project presents the production of Z-olefins through rhodium-catalyzed hydrofunctionalization using the starting materials, dienes and aldehydes. This method requires an inert atmosphere and the reaction progress can be monitored by Nuclear Magnetic Resonance (NMR) using an internal standard to quantify the amount of product formed. In this process, it was observed that the starting material was consumed until more than 95% conversion. In addition, the possibility of using different dienes, such as diene esters and phenyl dienes, as well as different aldehydes could further broaden the scope of this method. The usefulness of this process can be applied to the production of complex molecules. For example, in the synthesis of a glucagon receptor antagonist, which is a drug that is used in the treatment of diabetes. Currently, there is a limited number of methods used to create Z-olefins; however, this proven procedure can be further applied in other hydrofunctionalization

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36

Wrackmeyera, Bernd, Sergej V. Gruener, and Alla S. Zolotareva. "Reactivity of Alkoxyethynyl(trimethyl)silane, -germane and -stannane towards Trialkylboranes. Organometallic-Substituted Enol Ethers." Zeitschrift für Naturforschung B 58, no. 11 (November 1, 2003): 1035–40. http://dx.doi.org/10.1515/znb-2003-1101.

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Abstract Methoxyethynyl(trimethyl)silane (1a) reacts at 100°C very slowly with triethylborane (4) to give a mixture of alkenes, one of which is the 1,1-organoboration product (Z)-1-methoxy-1-trimethylsilyl- 2-diethylboryl-but-1-ene (7a). Methoxyethynyl(trimethyl)germane (2a) reacts within minutes at 60 - 70°C with 4, tripropylborane (5) and 9-ethyl-9-borabicyclo[3.3.1]nonane (6) by 1,1-organoboration in the usual regio- and stereospecific way to give the corresponding alkenes (9a - 11a). The analogous reactions of the ethoxyethynyl(trimethyl)germane (2b) require longer heating and are accompanied by decomposition of 2b. Ethoxyethynyl(trimethyl)stannane (3b) reacts with the trialkylboranes 4- 6 already below room temperature by 1,1-organoboration to give the alkenes (12b - 14b) in quantitative yield. The compound 3b also reacts with the alkenes, e.g. 9a, 13b, 14b, to give novel organometallicsubstituted dienes. All products were characterised by multinuclear magnetic resonance spectroscopy (1H, 11B, 13C, 29Si, and 119Sn NMR).

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37

Moberg, Christina. "Silylboranes as Powerful Tools in Organic Synthesis: Stereo- and Regioselective Reactions with 1,n-Enynes." Synthesis 52, no. 21 (August 20, 2020): 3129–39. http://dx.doi.org/10.1055/s-0040-1707247.

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Bismetalated alkenes, accessible by element–element addition to alkynes, are valuable building blocks in organic synthesis, providing wide opportunities for divergent synthesis. Silaboration of alkynes with a pendant olefinic group, catalyzed by group 10 metal complexes, and subsequent transformation of the silicon and boron functional groups give access to densely functionalized 1,3-dienes and 1,3,5-trienes with defined stereo- and regiochemistry, 1,2-dienes, and carbocyclic and heterocyclic products.1 Introduction2 Background3 Reactions with 1,3-Enynes4 Cyclization 1,6-Enynes5 Cyclization 1,7-Enynes6 Cyclization of 1,n-Enynes (n > 7)7 Cyclization of Dienynes and Enediynes8 Cyclization of 1,6-Diynes9 Conclusions

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38

Zard, Samir, та Raphaël Simonet-Davin. "A Direct Xanthate-Based Route to γ-Thiolactones". Synlett 29, № 06 (2 січня 2018): 815–19. http://dx.doi.org/10.1055/s-0036-1590987.

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The first examples of direct synthesis of γ-thiolactones by addition of a thiolactone-based radical are described. Mono- and bis-γ-thiolactones can be obtained by a dilauroyl peroxide initiated addition of thiolactone xanthate to various alkenes and α,ω-dienes. The process is modular and exhibits a high functional group tolerance.

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39

Zhao, Zhijun, Samir Husainy, and Geoffrey D. Smith. "Kinetics Studies of the Gas-Phase Reactions of NO3Radicals with Series of 1-Alkenes, Dienes, Cycloalkenes, Alkenols, and Alkenals." Journal of Physical Chemistry A 115, no. 44 (November 10, 2011): 12161–72. http://dx.doi.org/10.1021/jp206899w.

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40

Kurkutov, Evgeny O., and Bagrat A. Shainyan. "Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium." Molecules 27, no. 19 (September 20, 2022): 6169. http://dx.doi.org/10.3390/molecules27196169.

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A one-pot synthesis of linear and cyclic β-alkoxyselenides is developed through the iodine-mediated three-component reaction of elemental selenium with alkenes (dienes) and alcohols. Selenylation of 1,5-hexadiene gives 2,5-di(methoxymethyl)tetrahydroselenophene and 2-methoxy-6-(methoxymethyl)tetrahydro-2H-selenopyran via the 5-exo-trig and 6-endo-trig cyclization. 1,7-Octadiene affords only linear 1:2 adduct with two terminal double bonds. 1,5-Cyclooctadiene results in one diastereomer of 2,6-dialkoxy-9-selenabicyclo [3.3.1]nonanes via 6-exo-trig cyclization. With 1,3-diethenyl-1,1,3,3-tetramethyldisiloxane, the first ring-substituted representative of a very rare class of heterocycles, 1,4,2,6-oxaselenadisilinanes, was obtained at a high yield.

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41

Rocard, Lou, Donghuang Chen, Adrien Stadler, Hailong Zhang, Richard Gil, Sophie Bezzenine, and Jerome Hannedouche. "Earth-Abundant 3d Transition Metal Catalysts for Hydroalkoxylation and Hydroamination of Unactivated Alkenes." Catalysts 11, no. 6 (May 25, 2021): 674. http://dx.doi.org/10.3390/catal11060674.

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This review summarizes the most noteworthy achievements in the field of C–O and C–N bond formation by hydroalkoxylation and hydroamination reactions on unactivated alkenes (including 1,2- and 1,3-dienes) promoted by earth-abundant 3d transition metal catalysts based on manganese, iron, cobalt, nickel, copper and zinc. The relevant literature from 2012 until early 2021 has been covered.

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42

Arnold, Donald R., and Kimberly A. McManus. "Photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction: methanol, beta-myrcene, and 1,4-dicyanobenzene. Intramolecular cyclization of an ene-diene radical cation." Canadian Journal of Chemistry 76, no. 9 (September 1, 1998): 1238–48. http://dx.doi.org/10.1139/v98-156.

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The photochemical nucleophile-olefin combination, aromatic substitution (photo-NOCAS) reaction of methanol, 7-methyl-3-methylene-1,6-octadiene ( β-myrcene, 1), and 1,4-dicyanobenzene yields five 1:1:1 adducts:cis-2-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylenecyclohexane (15), trans-2-(4-cyanophenyl)-4-(1-methoxy-1-methylethyl)-1-methylenecyclohexane (16), 1-(4-cyanophenylmethyl)-4-(1-methoxy-1-methylethyl)cyclohexene (17), 4-[4-methoxy-3,3-dimethylcyclohex-(E)-1-ylidenyl]methylbenzonitrile (18), and 4-(1-vinyl-4-trans-methoxy-3,3-dimethylcyclohexyl)benzonitrile (19). All of these adducts are cyclic; variation in the product ratio as a function of methanol concentration indicates cyclization is occurring, 1,6-endo, with both the initially formed radical cation and with the intermediate β-alkoxyalkyl radicals. Evidence based upon comparison of the ionization and oxidation potential of β-myrcene with model alkenes and with conjugated dienes indicates the initial electron transfer involves the trisubstituted mono alkene moiety; the diene moiety, mono-substituted at a nodal position, has a higher oxidation potential. High-level ab initio molecular orbital calculations (MP2/6-31G*//HF/6-31G*) provide useful information regarding the nature (relative energies and charge and spin distribution) of the intermediate radical cations, which supports the proposed reaction mechanism. Key words: photoinduced electron transfer, radicals, radical cations, β-myrcene, cyclization.

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43

Lewis, Frederick D., and Eric Weitz. "Selective isomerization of alkenes, dienes, and trienes with infrared lasers." Accounts of Chemical Research 18, no. 6 (June 1985): 188–94. http://dx.doi.org/10.1021/ar00114a005.

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44

St. John Foreman, Mark R., Alexandra M. Z. Slawin, and J. Derek Woollins. "The reaction of dithiadiphosphetane disulfides with dienes, alkenes and thioaldehydes." Journal of the Chemical Society, Dalton Transactions, no. 7 (1999): 1175–84. http://dx.doi.org/10.1039/a808918c.

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45

Lee, Vladimir Ya. "Organogermanium Analogues of Alkenes, Alkynes, 1,3-Dienes, Allenes, and Vinylidenes." Molecules 28, no. 4 (February 6, 2023): 1558. http://dx.doi.org/10.3390/molecules28041558.

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In this review, the latest achievements in the field of multiply bonded organogermanium derivatives, mostly reported within the last two decades, are presented. The isolable Ge-containing analogues of alkenes, alkynes, 1,3-dienes, allenes, and vinylidenes are discussed, and for each class of unsaturated organogermanium compounds, the most representative examples are given. The synthetic approaches toward homonuclear multiply bonded combinations solely consisting of germanium atoms, and their heteronuclear variants containing germanium and other group 14 elements, both acyclic and cyclic, are discussed. The peculiar structural features and nonclassical bonding nature of the abovementioned compounds are discussed based on their spectroscopic and structural characteristics, in particular their crystallographic parameters (double bond length, trans-bending at the doubly bonded centers, and twisting about the double bond). The prospects for the practical use of the title compounds in synthetic and catalytic fields are also briefly discussed.

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46

CHAMBERS, R. D., S. L. JONES, S. J. MULLINS, A. SWALES, P. TELFORD, and M. L. H. WEST. "ChemInform Abstract: Perfluorinated Alkenes and Dienes in a Diverse Chemistry." ChemInform 22, no. 38 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199138315.

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47

Jiang, Zhiwei, Longlei Hou, Chunjie Ni, Jiangfei Chen, Dong Wang, and Xiaofeng Tong. "Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes." Chemical Communications 53, no. 30 (2017): 4270–73. http://dx.doi.org/10.1039/c7cc01488k.

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The Pd(0)-catalyzed asymmetric vinylborylation of (Z)-1-iodo-dienes with B₂pin₂ is reported, which provides access to 3,3-disubstituted tetrahydropyridine with excellent enantioselectivity.

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48

Vogel, Pierre, Maris Turks, Laure Bouchez, Cotinica Craita, M. Carmen Murcia, Freddy Fonquerne, Charles Didier, Xiaogen Huang, and Christopher Flowers. "Use of sultines in the asymmetric synthesis of polypropionate antibiotics." Pure and Applied Chemistry 80, no. 4 (January 1, 2008): 791–805. http://dx.doi.org/10.1351/pac200880040791.

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At low temperature and in the presence of an acid catalyst, SO2 adds to 1,3-dienes equilibrating with the corresponding 3,6-dihydro-1,2-oxathiin-2-oxides (sultines). These compounds are unstable above -60 °C and equilibrate with the more stable 2,5-dihydrothiophene 1,1-dioxides (sulfolenes). The hetero-Diels-Alder additions of SO2 are suprafacial and follow the Alder endo rule. The sultines derived from 1-oxy-substituted and 1,3-dioxy-disubstituted 1,3-dienes cannot be observed at -100 °C but are believed to be formed faster than the corresponding sulfolenes. In the presence of acid catalysts, the 6-oxy-substituted sultines equilibrate with zwitterionic species that react with electron-rich alkenes such as enoxysilanes and allylsilanes, generating β,γ-unsaturated silyl sulfinates that can be desilylated and desulfinylated to generate polypropionate fragments containing up to three contiguous stereogenic centers and an (E)-alkene unit. Alternatively, the silyl sulfinates can be reacted with electrophiles to generate polyfunctional sulfones (one-pot, four-component synthesis of sulfones), or oxidized into sulfonyl chlorides and reacted with amines, then realizing a one-pot, four-component synthesis of polyfunctional sulfonamides. Using enantiomerically enriched dienes such as 1-[(R)- or 1-(S)-phenylethyloxy]-2-methyl-(E,E)-penta-1,3-dien-3-yl isobutyrate, derived from inexpensive (R)- or (S)-1-phenylethanol, enantiomerically enriched stereotriads are obtained in one-pot operations. The latter are ready for further chain elongation. This has permitted the development of expeditious total asymmetric syntheses of important natural products of biological interest such as the baconipyrones, rifamycin S, and apoptolidin A.

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49

Gulías, Moisés, Fernando López, and José L. Mascareñas. "Development of transition-metal-catalyzed cycloaddition reactions leading to polycarbocyclic systems." Pure and Applied Chemistry 83, no. 3 (February 7, 2011): 495–506. http://dx.doi.org/10.1351/pac-con-10-10-23.

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We present a compilation of methodologies developed in our laboratories to assemble polycyclic structures containing small- and medium-sized cycles, relying on the use of transition-metal-catalyzed (TMC) cycloadditions. First, we discuss the use of alkylidenecyclopropanes (ACPs) as 3C-atom partners, in particular in their Pd-catalyzed (3 + 2) cycloadditions with alkynes, alkenes, and allenes, reactions that lead to cyclopentane-containing polycyclic products in excellent yields. Then, we present the expansion of this chemistry to a (4 + 3) annulation with conjugated dienes, and to inter- and intramolecular (3 + 2 + 2) cycloadditions using external alkenes as additional 2C-π-systems. These reactions allow the preparation of different types of polycyclic structures containing cycloheptene rings, the topology of the products depending on the use of Pd or Ni catalysts. Finally, we include our more recent discoveries on the development of (4 + 3) and (4 + 2) intramolecular cyclo-additions of allenes and dienes, promoted by Pt and Au catalysts, and discuss mechanistic insights supported by experimental and density functional theory (DFT) calculations. An enantioselective version of the (4 + 2) cycloaddition with phosphoramidite Au(I) catalysts is also presented.

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50

Shainyan, Bagrat A., Mikhail Yu Moskalik, Vera V. Astakhova, Irina V. Sterkhova, and Igor A. Ushakov. "ChemInform Abstract: Oxidative Addition of Trifluoroacetamide to Alkenes, 2,5-Dimethylhexa-2,4-diene and Conjugated Cyclic Dienes." ChemInform 47, no. 5 (January 2016): no. http://dx.doi.org/10.1002/chin.201605077.

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