REACTIONS OF O,O'-DISUBSTITUTED BENZONITRILE OXIDES WITH 8-AZAHEPTAFULVENES

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 mixt ure of equilibrating ''fused'' and ''spiro'' adducts (3/4)] and on the C-2-C-3 double bond (to give 12 which isomerizes to 13) of 2. Site se lectivity was highly enhanced by carrying out the reaction in polar so lvents. Only the attack on the C=N moiety was observed in the polar an d protic methanol. A synthesis of 13 by a mild new procedure of decomp lexation of the tricarbonyliron complex of 12 (i.e., 15) is described.