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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2006 Volume 16, Issue 5, Pages 276–278 (Mi mendc3622)

This article is cited in 7 papers

3-Methylcyclopropene-3-carbonitrile as a new enophile of the Alder-ene reaction

R. V. Ashirova, S. A. Appolonovab, G. A. Shamovc, V. V. Plemenkova

a Kazan State Medical University, Kazan, Russian Federation
b FSUE 'Antidope Centre', Moscow, Russian Federation
c Division of Informational Technologies, Kazan Scientific Centre of the Russian Academy of Sciences, Kazan, Russian Federation

Abstract: By the reactions of 3-methylcyclopropene-3-carbonitrile with methylenecyclohexane, α-methylstyrene and β-pinene products of their cyclopropanation have been obtained, the formation of the latter proceeding by the Alder-ene addition scheme. A DFT study of the reaction mechanism shows that most favourable are exo transition states with syn configuration of the CN group and the ene moiety.

Language: English

DOI: 10.1070/MC2006v016n05ABEH002328



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