RITTER REACTION ON TERPENOIDS .4. REMARKABLE TENDENCY TO PRODUCE 3-AZA-BICYCLO[3.3.1]NON-2-ENE SYSTEMS FROM MONO AND SESQUITERPENES

Reaction of cyclic and acyclic monoterpenes with acetonitrile under Ri tter type conditions was investigated. An unusual tendency to obtain r acemic 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo [3.3.1] non-2-ene perchlorate was observed in all cases regardless of the starting terp ene, It is worthy to pointing out that when linear terpenes were used, the reaction is believed to follow a biomimetic pathway forming cycli c cationic species before reacting with the nitrile to form the same b yciclic frame. If 3,5-ditrifluoromethylbenzonitrile was employed the c orresponding isobomylamide derivative was obtained instead.