R. V. Ashirov, S. A. Appolonova, G. A. Shamov, V. V. Plemenkov, “3-Methylcyclopropene-3-carbonitrile as a new enophile of the Alder-ene reaction”, Mendeleev Commun., 2006, Volume 16, Issue 5,Pages <nobr>276

This article is cited in 7 papers

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

R. V. Ashirov^a, S. A. Appolonova^b, G. A. Shamov^c, V. V. Plemenkov^a

^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