Quantum Chemical Study of the Addition of Secondary Phosphine Chalcogenides to Vinyl Selenides

DFT quantum chemical calculations at the B3PW91/6-31G( d ) level of theory have shown that the addition of secondary phosphine sulfides and phosphine selenides with alkyl, phenyl, and phenylalkyl substituents to pentyl vinyl and hexyl vinyl selenides follows a molecular mechanism against the Markovn...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2020-10, Vol.56 (10), p.1696-1701
Main Authors: Vereshchagina, Ya. A., Ismagilova, R. R., Chachkov, D. V., Chernysheva, N. A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:DFT quantum chemical calculations at the B3PW91/6-31G( d ) level of theory have shown that the addition of secondary phosphine sulfides and phosphine selenides with alkyl, phenyl, and phenylalkyl substituents to pentyl vinyl and hexyl vinyl selenides follows a molecular mechanism against the Markovnikov rule through energetically favorable eight-membered transition state, leading to the formation of tertiary phosphine chalcogenides. Secondary phosphine selenides are more reactive than the corresponding phosphine sulfides.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428020100048