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Paper | Special issue | Vol 47, No. 1, 1998, pp.453-468
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)76
Reactions of O,O'-Disubstituted Benzonitrile Oxides with 8-Azaheptafulvenes

Mauro Freccero, Remo Gandolfi,* and Mirko Sarzi Amade'

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

Abstract

In the reaction of O,O’-disubstituted benzonitrile oxides (1f-h) with 8-p-tolyl-8-azaheptafulvene (2) in cyclohexane there is a competition between attack by the nitrile oxides on the C=N moiety [to give a mixture of equilibrating “fused” and “spiro” adducts (3/4)] and on the C2-C3 double bond (to give 12 which isomerizes to 13) of 2. Site selectivity was highly enhanced by carrying out the reaction in polar solvents. Only the attack on the C=N moiety was observed in the polar and protic methanol. A synthesis of 13 by a mild new procedure of decomplexation of the tricarbonyliron complex of 12 (i.e., 15) is described.