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Communication | Regular issue | Vol 12, No. 7, 1979, pp.897-902
Published online, 1st January, 1970
DOI: 10.3987/R-1979-07-0897
Syn Selectivity in the Reactions of Azomethiene Imines and Azomethine Oxides with cis-3,4-Disubstituted Cyclobutenes

Remo Gandolfi,* Missimo Ratti, Lucio Toma, and Carlo De Micheli

*Dipartamento di Chimica Organica, Università di Pavia, V. le Taramelli 10, 27100 Pavia, Italy

Abstract

3,4-Dihydroisoquinoline-N-phenylimine reacted with cis-3,4-dichloro, -dihydroxy and -diacetoxycyclobutenes to give the sterically disfavoured syn adducts as dominant products; with carbonyldioxy and dicarbomethoxycyclobutenes repulsive steric interactions led to the prevailence of the anti adducts. An increased syn selectivity was found for the reactions of 3,4-dihydroisoquinoline-N-oxide with diacetoxycyclobutene and of nitro substituted 3,4-dihydroisoquinoline-N-phenylimines with dichlorocyclobutene.