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Статті в журналах з теми "Radical rearrangement"

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Автор: Grafiati

Опубліковано: 10 грудня 2022

Оновлено: 28 січня 2023

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1

Greaney, Michael F., and David M. Whalley. "Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation." Synthesis 54, no. 08 (December 1, 2021): 1908–18. http://dx.doi.org/10.1055/a-1710-6289.

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Анотація:

AbstractThe Smiles rearrangement has undergone a renaissance in recent years providing new avenues for non-canonical arylation techniques in both the radical and polar regimes. This short review will discuss recent applications of the reaction (from 2017 to late 2021), including its relevance to areas such as heterocycle synthesis and the functionalization of alkenes and alkynes as well as glimpses at new directions for the field.1 Introduction2 Polar Smiles Rearrangements3 Radical Smiles: Alkene and Alkyne Functionalization4 Radical Smiles: Rearrangements via C–X Bond Cleavage5 Radical Smiles: Miscellaneous Rearrangements6 Conclusions

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2

Kolodziejczak, Krystian, Alexander J. Stewart, Tell Tuttle, and John A. Murphy. "Radical and Ionic Mechanisms in Rearrangements of o-Tolyl Aryl Ethers and Amines Initiated by the Grubbs–Stoltz Reagent, Et3SiH/KOtBu." Molecules 26, no. 22 (November 15, 2021): 6879. http://dx.doi.org/10.3390/molecules26226879.

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Анотація:

Rearrangements of o-tolyl aryl ethers, amines, and sulfides with the Grubbs–Stoltz reagent (Et3SiH + KOtBu) were recently announced, in which the ethers were converted to o-hydroxydiarylmethanes, while the (o-tol)(Ar)NH amines were transformed into dihydroacridines. Radical mechanisms were proposed, based on prior evidence for triethylsilyl radicals in this reagent system. A detailed computational investigation of the rearrangements of the aryl tolyl ethers now instead supports an anionic Truce–Smiles rearrangement, where the initial benzyl anion can be formed by either of two pathways: (i) direct deprotonation of the tolyl methyl group under basic conditions or (ii) electron transfer to an initially formed benzyl radical. By contrast, the rearrangements of o-tolyl aryl amines depend on the nature of the amine. Secondary amines undergo deprotonation of the N-H followed by a radical rearrangement, to form dihydroacridines, while tertiary amines form both dihydroacridines and diarylmethanes through radical and/or anionic pathways. Overall, this study highlights the competition between the reactive intermediates formed by the Et3SiH/KOtBu system.

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3

Flintoft, Louisa. "A radical rearrangement." Nature Reviews Genetics 9, no. 1 (January 2008): 5. http://dx.doi.org/10.1038/nrg2292.

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4

Merkley, Nadine, Paul C. Venneri, and John Warkentin. "Cyclopropanation of benzylidenemalononitrile with dialkoxycarbenes and free radical rearrangement of the cyclopropanes." Canadian Journal of Chemistry 79, no. 3 (March 1, 2001): 312–18. http://dx.doi.org/10.1139/v01-017.

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Анотація:

Thermolysis of 2-cinnamyloxy-2-methoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline (1a) and the analogous 2-benzyloxy-2-methoxy compound (1b) at 110°C, in benzene containing benzylidenemalononitrile, afforded products of apparent regiospecific addition of methoxycarbonyl and cinnamyl (or benzyl) radicals to the double bond. When the thermolysis of 1a was run with added TEMPO, methoxycarbonyl and cinnamyl radicals were captured. Thermolysis of the 2,2-dibenzyloxy analogue (1c) in the presence of benzylidenemalononitrile gave an adduct that is formally the product of addition of benzyloxycarbonyl and benzyl radicals to the double bond. In this case, a radical addition mechanism could be ruled out, because the rate constant for decarboxylation of benzyloxycarbonyl radicals is very large. A mechanism that fits all of the results is predominant cyclopropanation of benzylidenemalononitrile by the dialkoxycarbenes derived from the oxadiazolines, in competition with fragmentation of the carbenes to radical pairs. The cyclopropanes so formed then undergo homolytic ring-opening to the appropriate diradicals. Subsequent β-scission of the diradicals to afford radical pairs, and coupling of those pairs, gives the final products. Thus, both carbene and radical chemistry are involved in the overall processes.Key words: cyclopropane, dialkoxycarbene, β-scission, oxadiazoline, radical.

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5

Davies, M. J., S. Fu, and R. T. Dean. "Protein hydroperoxides can give rise to reactive free radicals." Biochemical Journal 305, no. 2 (January 15, 1995): 643–49. http://dx.doi.org/10.1042/bj3050643.

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Proteins damaged by free-radical-generating systems in the presence of oxygen yield relatively long-lived protein hydroperoxides. These hydroperoxides have been shown by e.p.r. spectroscopy to be readily degraded to reactive free radicals on reaction with iron(II) complexes. Comparison of the observed spectra with those obtained with free amino acid hydroperoxides had allowed identification of some of the protein-derived radical species (including a number of carbon-centred radicals, alkoxyl radicals and a species believed to be the CO2 radical anion) and the elucidation of novel fragmentation and rearrangement processes involving amino acid side chains. In particular, degradation of hydroperoxide functions on the side chain of glutamic acid is shown to result in decarboxylation at the side-chain carboxy group via the formation of the CO2 radical anion; the generation of an identical radical from hydroperoxide groups on proteins suggests that a similar process occurs with these molecules. In a number of cases these fragmentation and rearrangement reactions give rise to further reactive free radicals (R., O2-./HO2., CO2-.) which may act as chain-carrying species in protein oxidations. These studies suggest that protein hydroperoxides are capable of initiating further radical chain reactions both intra- and inter-molecularly, and provide information on some of the fundamental mechanisms of protein alteration and side-chain fragmentation.

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6

Allart-Simon, Ingrid, Stéphane Gérard, and Janos Sapi. "Radical Smiles Rearrangement: An Update." Molecules 21, no. 7 (July 6, 2016): 878. http://dx.doi.org/10.3390/molecules21070878.

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7

Quiclet-Sire, Béatrice, and Samir Z. Zard. "A radical thia-Brook rearrangement." Chemical Communications 50, no. 45 (2014): 5990. http://dx.doi.org/10.1039/c4cc01683a.

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8

Bacqué, Eric, Myriem El Qacemi, and Samir Z. Zard. "An Unusual Radical Smiles Rearrangement." Organic Letters 7, no. 17 (August 2005): 3817–20. http://dx.doi.org/10.1021/ol051568l.

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9

Reynolds, Dan W., Bijan Harirchian, Huh-Sun Chiou, B. Kaye Marsh, and Nathan L. Bauld. "The cation radical vinylcyclobutane rearrangement." Journal of Physical Organic Chemistry 2, no. 1 (January 1989): 57–88. http://dx.doi.org/10.1002/poc.610020108.

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10

Tappin, Nicholas D. C., and Philippe Renaud. "Radical Reactions of Boron-Ate Complexes Promoting a 1,2-Metallate Rearrangement." CHIMIA International Journal for Chemistry 74, no. 1 (February 26, 2020): 33–38. http://dx.doi.org/10.2533/chimia.2020.33.

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Анотація:

Recently there has been an explosion of interest in the synthetic community for the addition of radicals into unsaturated organoboron-ate complexes. This review will give a concise outline for radical processes involving boron-ate complexes which trigger a subsequent anionotropic rearrangement.

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11

Chow, Y. L., and Xianen Cheng. "1,3-Diketonatoboron difluoride sensitized cation radical reactions." Canadian Journal of Chemistry 69, no. 8 (August 1, 1991): 1331–36. http://dx.doi.org/10.1139/v91-198.

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Анотація:

Dibenzoylmethanatoboron difluoride (DBMBF2) and allied BF2 complexes interact from their singlet excited state with trans-anethole (t-A), quadricyclene (QC), and norbornadiene (NBD) by electron transfer to generate the corresponding cation radicals, which undergo the reported reactions. By sensitization, t-A undergoes dimerization to form the anti head-to-head and syn head-to-head dimers with retention of stereochemistry. The formation is reversible under sensitization conditions, leading to accumulation of the more stable anti isomer. However, irradiation of the absorption band of the DBMBF2 – t-A ground state complex did not lead to dimerization of t-A. By DBMBF2 sensitization, QC is cleanly converted to NBD while NBD is not affected. The calculation shows QC+• possesses higher energy than NBD+• by 7.5 kcal/mol, hence an irreversible rearrangement. Other sensitizers (e.g., cyanoaromatics and tetrachlorobenzoquinone) also promote these cation radical reactions but not as cleanly as DBMBF2. Key words: photosensitization by boron complexes, cation radical rearrangement, cation radical cycloaddition, electron transfer sensitization, photoreaction of ground state complexes.

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12

ROTA, Cristina, P. David BARR, V. Martha MARTIN, F. Peter GUENGERICH, Aldo TOMASI, and P. Ronald MASON. "Detection of free radicals produced from the reaction of cytochrome P-450 with linoleic acid hydroperoxide." Biochemical Journal 328, no. 2 (December 1, 1997): 565–71. http://dx.doi.org/10.1042/bj3280565.

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Анотація:

The ESR spin-trapping technique was employed to investigate the reaction of rabbit cytochrome P-450 1A2 (P450) with linoleic acid hydroperoxide. This system was compared with chemical systems where FeSO4 or FeCl3 was used in place of P450. The spin trap 5,5ʹ-dimethyl-1-pyrroline N-oxide (DMPO) was employed to detect and identify radical species. The DMPO adducts of hydroxyl, O2-•, peroxyl, methyl and acyl radicals were detected in the P450 system. The reaction did not require NADPH-cytochrome P-450 reductase or NADPH. The same DMPO-radical adducts were detected in the FeSO4 system. Only DMPO-•OH radical adduct and carbon-centred radical adducts were detected in the FeCl3 system. Peroxyl radical production was completely O2-dependent. We propose that polyunsaturated fatty acids are initially reduced to form alkoxyl radicals, which then undergo intramolecular rearrangement to form epoxyalkyl radicals. Each epoxyalkyl radical reacts with O2, forming a peroxyl radical. Subsequent unimolecular decomposition of this peroxyl radical eliminates O2-• radical.

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13

Crich, David, and Qingwei Yao. "The .beta.-(phosphonooxy)alkyl radical rearrangement." Journal of the American Chemical Society 115, no. 3 (February 1993): 1165–66. http://dx.doi.org/10.1021/ja00056a060.

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14

de Sanabia, J. Arce, and Arturo E. Carrión. "Radical cation catalyzed pinacol-pinacolone rearrangement." Tetrahedron Letters 34, no. 49 (December 1993): 7837–40. http://dx.doi.org/10.1016/s0040-4039(00)61489-2.

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15

Krishnamurthy, Venkat, and Viresh H. Rawal. "Kinetics of the Oxiranylcarbinyl Radical Rearrangement." Journal of Organic Chemistry 62, no. 6 (March 1997): 1572–73. http://dx.doi.org/10.1021/jo962054q.

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16

Crich, David, та Dae-Hwan Suk. "The β-(acyloxy)alkyl radical rearrangement revisited". Canadian Journal of Chemistry 82, № 2 (1 лютого 2004): 75–79. http://dx.doi.org/10.1139/v03-148.

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Анотація:

A β-(acyloxy)alkyl radical precursor, containing a carboxylate residue suitably placed for the trapping of any intermediate alkene radical cations, has been constructed. In nonpolar solutions the probe, in the form of either the free acid or its tetrabutylammonium salt, undergoes the typical rearrangement reaction with no evidence of trapping, leading to the conclusion that the reaction is either concerted or that collapse of any intermediate contact ion pair is so rapid as to preclude the possibility of trapping.Key words: radical, rearrangement, contact ion pair.

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17

Schöneich, Christian. "Radical rearrangement and transfer reactions in proteins." Essays in Biochemistry 64, no. 1 (January 10, 2020): 87–96. http://dx.doi.org/10.1042/ebc20190046.

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Анотація:

Abstract Radical rearrangement and transfer reactions play an important role in the chemical modifications of proteins in vivo and in vitro. These reactions depend on protein sequence, as well as structure and dynamics. Frequently, these reactions have well-defined precedents in the organic chemistry literature, but their occurrence in proteins provides a stage for a number of novel and, perhaps, unexpected reaction products. This essay will provide an overview over a few representative examples of radical rearrangement and transfer reactions.

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18

NISHIDA, A., and M. NISHIDA. "ChemInform Abstract: Development of New Radical Reactions: Skeletal Rearrangement via Alkoxy Radicals and Asymmetric Radical Cyclization." ChemInform 28, no. 41 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199741350.

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19

Pudlo, Marc, Ingrid Allart-Simon, Bernard Tinant, Stéphane Gérard, and Janos Sapi. "First domino radical cyclisation/Smiles rearrangement combination." Chemical Communications 48, no. 18 (2012): 2442. http://dx.doi.org/10.1039/c2cc15670a.

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20

Jurczak, M. "Radical Induced Isoxazolidine-Isoxazolidin-5-one Rearrangement." Synlett 1999, no. 1 (January 1999): 79–80. http://dx.doi.org/10.1055/s-1999-2526.

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21

Dowd, Paul, Wei Zhang, and Khalid Mahmood. "A cyclobutanone-based tandem free radical rearrangement." Tetrahedron Letters 35, no. 31 (August 1994): 5563–66. http://dx.doi.org/10.1016/s0040-4039(00)77247-9.

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22

Quiclet-Sire, Beatrice, and Samir Z. Zard. "ChemInform Abstract: A Radical Thia-Brook Rearrangement." ChemInform 45, no. 40 (September 18, 2014): no. http://dx.doi.org/10.1002/chin.201440191.

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23

Bestari, Ketut, Richard T. Oakley, and A. Wallace Cordes. "Skeletal scrambling of sulphur diimide radical anions." Canadian Journal of Chemistry 69, no. 1 (January 1, 1991): 94–99. http://dx.doi.org/10.1139/v91-014.

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Анотація:

In the presence of a catalytic quantity of alkali metal mixtures of sulphur diimides RNSNR and R′NSNR′(R, R′ = Ph, 4-C6H4Me, 4-C6H4OMe, SiMe3, SPh) undergo a rapid scrambling of the R and R′ groups. When R and R′ are significantly different (e.g., R = Ph, R′ = SiMe3 or SPh) the equilibrium is shifted to favour the unsymmetrical sulphur dimmide (R ≠ R′); the procedure thus represents an effective method for preparing such derivatives. A mechanism involving the centrosymmetric association and rearrangement of two sulphur diimide radical anions is suggested for the observed ligand scrambling. The synthesis and X-ray structure determination of the mixed diimide (4-NO2C6H4)SNSN(4-C6H4OMe) is reported. The crystals are monoclinic, space group P21/n; the molecules stack as plates along the a axis in a head-to-head fashion, producing an interplanar spacing between consecutive S2N2 units of 3.421 Å. Key words: sulphur diimide radical anions, skeletal rearrangements, (4-C6H4NO2)SNSN(4-C6H4OMe), X-ray structure.

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24

Kippo, Takashi, Kanako Hamaoka, and Ilhyong Ryu. "Bromine Radical-Mediated Sequential Radical Rearrangement and Addition Reaction of Alkylidenecyclopropanes." Journal of the American Chemical Society 135, no. 2 (December 28, 2012): 632–35. http://dx.doi.org/10.1021/ja311821h.

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25

Kourdioukov, Alexandre I. "Comparative DFT study of triplet and singlet elementary oxidation acts of the cyclohexane and 1,3-cyclohexadiene initiated by primary interaction with 3O2 under SCF conditions." Butlerov Communications 60, no. 11 (November 30, 2019): 128–42. http://dx.doi.org/10.37952/roi-jbc-01/19-60-11-128.

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Анотація:

The primary stages of the oxidation of model cyclohexane and 1,3-cyclohexadiene by triplet molecular oxygen and subsequent transformations involving triplet and singlet states were studied for the first time by the DFT method with the density functional B3LYP with the basis set 6-311++g(df,p). It was shown that, ceteris paribus, cyclohexane and 1,3-cyclohexadiene will be orders of magnitude more reactive compared to the activity of acyclic saturated hydrocarbons under SCF conditions when the oxidation process is initiated by the primary reaction with 3O2, which allows the propane-butane mixture to be effectively used as SCF conditions of heavy oils and use air purge to activate this process. The triplet associate complexes resulting from the oxidative cleavage of the secondary C–H bond of cyclohexane and 1,3-cyclohexadiene consist of hydrogen-bonded hydroperoxyl radical and cyclohexyl radical or 1,3-cyclohexadiene radical, respectively. These complexes can dissociate into unbound pairs of radicals, and therefore further reactions can proceed in the triplet or singlet direction. The singlet direction is characterized by hydrate-induced hydroperoxide-carbonyl transformation, as well as other hydrate-induced rearrangements. The triplet direction is characterized by the occurrence of triplet rearrangement, which in its essence is a triplet recombination of associated radicals. Associate triplet complexes can be agents of radical hydroperoxyl and alkyl activity, as well as agents of radical hydroxyl and alkoxyl activity. Most oxidative dehydrogenation reactions are absolutely real under a number of conditions, namely, they must take place under SCF conditions, as well as in the presence of an excess of SCF solvent necessary for the effective shift of thermodynamic equilibrium towards the target products in accordance with the Le Chatelier principle.

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26

Tao, Xiangzhang, Shengyang Ni, Lingyu Kong, Yi Wang, and Yi Pan. "Radical boron migration of allylboronic esters." Chemical Science 13, no. 7 (2022): 1946–50. http://dx.doi.org/10.1039/d1sc06760e.

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Анотація:

A photocatalyzed 1,3-boron shift of allylboronic esters is reported. The atom-switch acrobatics proceeds via cascade 1,2-boron migrations and Smiles type rearrangement to furnish a variety of terminally functionalized alkyl boronates.

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27

Brachet, Etienne, Leyre Marzo, Mohamed Selkti, Burkhard König, and Philippe Belmont. "Visible light amination/Smiles cascade: access to phthalazine derivatives." Chemical Science 7, no. 8 (2016): 5002–6. http://dx.doi.org/10.1039/c6sc01095d.

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Анотація:

We report the synthesis of various phthalazines via a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical Smiles rearrangement.

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28

Bates, Gordon S., and S. Ramaswamy. "A formal [1,3] sigmatropic reaction involving free radical intermediates: a mechanistic investigation." Canadian Journal of Chemistry 63, no. 3 (March 1, 1985): 745–54. http://dx.doi.org/10.1139/v85-123.

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The quantitative isomerization of 2,2-bis(ethylthio)-3,3-dimethylpent-4-enal to 2,2-bis(ethylthio)-5-methylhex-4-enal was studied over the temperature range 130–170 °C. An investigation of the generality and specific mechanism of this formal [1,3] sigmatropic shift was conducted with six related compounds. The rearrangements were found to obey first-order kinetics, and on the basis of significant positive entropies of activation (52–106 J deg−1 mo−1), crossover and trapping experiments, and the lack of a solvent effect (decane vs. DMF), an intermolecular, free-radical chain pathway has been proposed for the isomerization. During the rearrangement of several of the compounds esr signals were observed that were consistent with the presence of the proposed free-radical intermediates. These esr signals have been computer simulated.

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29

Revol, Guillaume, Christian Fuchs, and Samir Z. Zard. "A short formal total synthesis of (±)-hirsutic acid." Canadian Journal of Chemistry 90, no. 11 (November 2012): 927–31. http://dx.doi.org/10.1139/v2012-037.

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Анотація:

A short formal total synthesis of (±)-hirsutic acid is described using a Claisen rearrangement and a radical cascade as the key steps. The radical sequence involves an intermolecular addition of a radical derived from a xanthate followed by a cyclization and transfer of the xanthate group.

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30

Yan, Wanying, and Huawen Huang. "Radical Smiles Rearrangement Enabling Migratory Reductive Cross Coupling." Chinese Journal of Organic Chemistry 41, no. 10 (2021): 4097. http://dx.doi.org/10.6023/cjoc202100074.

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31

Zona, Thomas A., and Joshua L. Goodman. "Stereospecific Hydrogen Rearrangement of a 1,4 Cation Radical." Journal of the American Chemical Society 117, no. 21 (May 1995): 5879–80. http://dx.doi.org/10.1021/ja00126a039.

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32

Watkins, Michael A., Eric D. Nelson, Shane E. Tichy, and Hilkka I. Kenttämaa. "Rearrangement of phenylcarbene radical cation to dehydrotropylium cation." International Journal of Mass Spectrometry 249-250 (March 2006): 1–7. http://dx.doi.org/10.1016/j.ijms.2006.01.024.

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33

Tada, Masaru, Kunimi Inoue, and Masami Okabe. "RADICAL REARRANGEMENT OF A THIOESTER MEDIATED BY COBALAMIN." Chemistry Letters 15, no. 5 (May 5, 1986): 703–4. http://dx.doi.org/10.1246/cl.1986.703.

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34

CRICH, D., та Q. YAO. "ChemInform Abstract: The β-(Phosphonooxy)alkyl Radical Rearrangement." ChemInform 24, № 24 (20 серпня 2010): no. http://dx.doi.org/10.1002/chin.199324228.

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35

DE SANABIA, J. A., and A. E. CARRION. "ChemInform Abstract: Radical Cation Catalyzed Pinacol-Pinacolone Rearrangement." ChemInform 25, no. 14 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199414143.

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36

Liu, Kai, Qiao Jin, Shuang Chen та Pei Nian Liu. "AgSCF3-mediated trifluoromethylthiolation of α,α-diaryl allylic alcohols via radical neophyl rearrangement". RSC Advances 7, № 3 (2017): 1546–52. http://dx.doi.org/10.1039/c6ra25378d.

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Анотація:

A novel example of AgSCF₃-mediated oxidative radical trifluoromethylthiolation of α,α-diaryl allylic alcohols is presented, producing various α-aryl-β-trifluoromethylthiolated carbonyl ketones via radical neophyl rearrangement under mild conditions.

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37

Xie, Lili, Xiaomeng Zhen, Shuping Huang, Xiaolong Su, Mai Lin та Yi Li. "Photoinduced rearrangement of vinyl tosylates to β-ketosulfones". Green Chemistry 19, № 15 (2017): 3530–34. http://dx.doi.org/10.1039/c7gc01467h.

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38

Tripathy, Alisha Rani, Girish Suresh Yedase, and Veera Reddy Yatham. "Cerium photocatalyzed radical smiles rearrangement of 2-aryloxybenzoic acids." RSC Advances 11, no. 41 (2021): 25207–10. http://dx.doi.org/10.1039/d1ra04130d.

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39

Beckwith, Athelstan L. J., та Peter J. Duggan. "The mechanism of the β-acyloxyalkyl radical rearrangement. Part 2: β-acyloxytetrahydropyranyl radicals". J. Chem. Soc., Perkin Trans. 2, № 9 (1993): 1673–79. http://dx.doi.org/10.1039/p29930001673.

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40

Wille, Uta, and Jilliarne Andropof. "Oxidation of Aromatic Alkynes with Nitrate Radicals (NO3•): An Experimental and Computational Study on a Synthetically Highly Versatile Radical." Australian Journal of Chemistry 60, no. 6 (2007): 420. http://dx.doi.org/10.1071/ch07045.

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Addition of electro- and photochemically generated nitrate radicals, NO3•, to the C≡C triple bond of aromatic alkynes 9a–9h leads to formation of 1,2-diketones 10a–10h. Surprisingly, benzophenones 11a–11h are obtained as by-products, which formally result from loss of a carbon atom. Density functional studies performed with the BHandHLYP method in combination with various basis sets revealed that 1,2-diketones result from 5-endo cyclization of the initially formed vinyl radical and loss of NO•. The key step to benzophenone formation is a γ-cleavage at the stage of the vinyl radical with release of NO2•, followed by Wolff rearrangement of the resulting α-oxo carbene.

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41

Wille, Uta, and Jilliarne Andropof. "Corrigendum to: Oxidation of Aromatic Alkynes with Nitrate Radicals (NO3•): An Experimental and Computational Study on a Synthetically Highly Versatile Radical." Australian Journal of Chemistry 60, no. 7 (2007): 547. http://dx.doi.org/10.1071/ch07045_co.

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Анотація:

Addition of electro- and photochemically generated nitrate radicals, NO3•, to the C≡C triple bond of aromatic alkynes 9a–9h leads to formation of 1,2-diketones 10a–10h. Surprisingly, benzophenones 11a–11h are obtained as by-products, which formally result from loss of a carbon atom. Density functional studies performed with the BHandHLYP method in combination with various basis sets revealed that 1,2-diketones result from 5-endo cyclization of the initially formed vinyl radical and loss of NO•. The key step to benzophenone formation is a γ-cleavage at the stage of the vinyl radical with release of NO2•, followed by Wolff rearrangement of the resulting α-oxo carbene.

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42

Zhao, Yan, Xiaomin Sun, Wenxing Wang, and Laixiang Xu. "Quantum chemical study on the atmospheric photooxidation of ethyl acetate." Canadian Journal of Chemistry 92, no. 9 (September 2014): 814–20. http://dx.doi.org/10.1139/cjc-2014-0199.

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The mechanism for OH radical initiated atmospheric photoxidation reaction of ethyl acetate was carried out by using the density functional theory method. Geometries have been optimized at the B3LYP level with a standard 6-31G(d,p) basis set. The single-point energy calculations have been performed at the MP2/6-31G(d), MP2/6-311++G(d,p), and CCSD(T)/6-31G(d) levels, respectively. All of the possible degradation channels involved in the oxidation of ethyl acetate by OH radicals have been presented and discussed. Among the five possible hydrogen abstraction pathways of the reaction of ethyl acetate with OH radicals, the hydrogen abstractions from the C1–H3 and C2–H5 bonds are the dominant reaction pathways due to the low potential barriers and strong exothermicity. The β-ester rearrangement of IM6 is energetically favorable but is not expected to be important. The α-ester rearrangement reaction and O2 direct abstraction from IM17 are the more favorable pathways and are strongly competitive. In addition, the α-ester rearrangement reaction is confirmed to be a one-step process. Acetic acid, formic acetic anhydride, acetoxyacetaldehyde, and acetic anhydride are the main products for the reaction of ethyl acetate with OH radicals.

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43

Guedes, Carmen L. B., Eduardo Di Mauro, Ariana De Campos, Leandro F. Mazzochin, Gislaine M. Bragagnolo, Fernando A. De Melo, and Marilene T. Piccinato. "EPR and Fluorescence Spectroscopy in the Photodegradation Study of Arabian and Colombian Crude Oils." International Journal of Photoenergy 2006 (2006): 1–6. http://dx.doi.org/10.1155/ijp/2006/48462.

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EPR and fluorescence spectroscopy were used to evaluate the degradation of crude oils of different origins that were submitted to photochemical weathering under tropical conditions. The EPR spectra obtained showed signals of the paramagnetic species: the vanadylVO2+ion and organic free radicals. A decrease in linewidth of free radical signals was observed for both oils irradiated for 100 hours with sunlight of 350 W/m2. The reduction in the linewidth of the free radical of 9.8% in Arabian oil and 18.5% in Colombian oil, as well as the decrease in radical numbers, indicated photochemical degradation, especially in Colombian oil. The linewidth narrowing corresponding to free radicals in the irradiated oils occurred due to the rearrangement among radicals and aromatic carbon consumption. The irradiated oils showed a reduction in the relative intensity of fluorescence of the aromatics with high molecular mass, polar aromatics, and asphaltene. The fluorescent fraction was reduced by 61% in Arabian oil and 72% in Colombian oil, corresponding to photochemical degradation of crude oil aromatic compounds.

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44

Jung, Hye Im, Yubin Kim та Dae Young Kim. "Electrochemical trifluoromethylation/semipinacol rearrangement sequences of alkenyl alcohols: synthesis of β-CF3-substituted ketones". Organic & Biomolecular Chemistry 17, № 13 (2019): 3319–23. http://dx.doi.org/10.1039/c9ob00373h.

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45

Kessabi, Fiona Murphy, Tammo Winkler, Jennifer A. R. Luft, and K. N. Houk. "Rearrangement of a Cyclohexyl Radical to a Cyclopentylmethyl Radical on the Avermectin Skeleton." Organic Letters 10, no. 11 (June 2008): 2255–58. http://dx.doi.org/10.1021/ol8001283.

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46

Kippo, Takashi, Kanako Hamaoka, and Ilhyong Ryu. "ChemInform Abstract: Bromine Radical-Mediated Sequential Radical Rearrangement and Addition Reaction of Alkylidenecyclopropanes." ChemInform 44, no. 29 (July 1, 2013): no. http://dx.doi.org/10.1002/chin.201329040.

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47

Desai, Nikunj, Daniel A. Thomas, Jungeun Lee, Jinshan Gao, and J. L. Beauchamp. "Eradicating mass spectrometric glycan rearrangement by utilizing free radicals." Chemical Science 7, no. 8 (2016): 5390–97. http://dx.doi.org/10.1039/c6sc01371f.

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48

Hossian, Asik, and Ranjan Jana. "Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement." Organic & Biomolecular Chemistry 14, no. 41 (2016): 9768–79. http://dx.doi.org/10.1039/c6ob01758d.

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A silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen is reported.

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49

Dolbier, William R., Keith W. Palmer, Feng Tian, Piotr Fiedorow, Andrzej Zaganiaczyk, and Henryk Koroniak. "[3,3] Sigmatropic Rearrangement of Some Fluorinated 1,5-Hexadienes." Collection of Czechoslovak Chemical Communications 67, no. 10 (2002): 1517–32. http://dx.doi.org/10.1135/cccc20021517.

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Fluorine atoms incorporated into 1,5-hexadiene molecule should influence the kinetic as well as the thermodynamic parameters of [3,3] sigmatropic rearrangement (Cope rearrangement). Within few decades is has been documented that this transformation proceeds in a concerted manner, rather than stepwise with some radical intermediates involved. Few new terminally fluorinated 1,5-hexadienes (compounds 3, 5A, 7, 9 and 5B) have been synthesized. The activation parameters of rearrangement have been determined and compared with those known for hydrocarbon analogues. While systems developing chair-like transition states (compounds 3 and 5) showed close similarity with hydrocarbon analogues (compound 1), those developing boat-like transition states (compounds 7, 9 and 5B) may proceed through radical stepwise mechanism. Computational studies of the transition states were carried out, showing that only ab initio methods (MP2 and especially DFT) can give approximate correlation with experimental data, whereas in the case of hydrocarbon analogues even simple semiempirical methods (AM1) were reliable enough to reproduce experimental results.

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50

Ren, Shichao, Chao Feng та Teck-Peng Loh. "Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones". Organic & Biomolecular Chemistry 13, № 18 (2015): 5105–9. http://dx.doi.org/10.1039/c5ob00632e.

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