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Effect of Cis/Trans Isomerism on Selective Oxidation of Olefins with Nitrous Oxide Full article

Journal Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416
Output data Year: 2016, Volume: 72, Number: 19, Pages: 2501-2506 Pages count : 6 DOI: 10.1016/j.tet.2016.03.084
Tags Cycloaddition, Isomers, Nitrous oxide, Olefins, Oxidation
Authors Ivanov Dmitry 1 , Babushkin Dmitry 1 , Semikolenov Sergey 1 , Malykhin Sergey 1,2 , Kharitonov Alexander 1 , Dubkov Konstantin 1
Affiliations
1 Boreskov Institute of Catalysis, Pr. Lavrentieva 5, 630090, Novosibirsk, Russia
2 Novosibirsk State University, Str. Pirogova 2, 630090, Novosibirsk, Russia

Funding (2)

1 Federal Agency for Scientific Organizations V.44.2.3.
2 Russian Foundation for Basic Research 14-03-31052

Abstract: Liquid phase oxidation of olefins with nitrous oxide is a promising synthetic route to ketones. The effect of cis/trans isomerism on the reactivity of olefins towards N2O and on the reaction mechanism was studied for the first time using 3-heptene oxidation as an example. Our experimental study revealed that cis- and trans-isomers of 3-heptene have similar reactivity and yield the same set of products. However, the cis/trans isomerism of the olefin has a pronounced effect on the reaction route involving the cleavage of the initial C]C bond and, accordingly, on the products ratio. The yield of ketones is lower for the transisomer due to higher contribution of the cleavage route.
Cite: Ivanov D. , Babushkin D. , Semikolenov S. , Malykhin S. , Kharitonov A. , Dubkov K.
Effect of Cis/Trans Isomerism on Selective Oxidation of Olefins with Nitrous Oxide
Tetrahedron. 2016. V.72. N19. P.2501-2506. DOI: 10.1016/j.tet.2016.03.084 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
Submitted: Jan 28, 2016
Accepted: Mar 24, 2016
Published online: Mar 26, 2016
Published print: May 12, 2016
Identifiers:
Web of science: WOS:000375164000017
Scopus: 2-s2.0-84962469702
Elibrary: 26983832
Chemical Abstracts: 2016:571786
Chemical Abstracts (print): 164:495594
OpenAlex: W2310850176
Citing:
DB Citing
Web of science 10
Scopus 11
Elibrary 11
OpenAlex 10
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