Ritter Reaction on Terpenoids. IV. Remarkable Tendency to Produce 3-Aza-bicyclo [3.3.1] non-2-ene Systems from Mono and Sesquiterpenes.

RODRIGUEZ, JUAN BAUTISTA; GROS, EDUARDO GERVASIO; CARAM, JOSÉ A.; MARSCHOFF, CARLOS M.

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Año: 1995 vol. 36 p. 7825 - 7828

0040-4039

Reaction of cyclic and acyclic monoterpenes with acetonitrile under Ritter type conditions was investigated. An unusual tendency to obtain racemic 8-acetamido-2,4,4,8-tetramethyl-3-aza-bicyclo[3.3.1] non-2-ene perchorate was observed in all cases regardless of the starting terpene. It is worthy to pointing out that when linear terpenes were used, the reaction is believed to follow a biomemitic pathway foeming cyclic cationic species before reacting with the nitrile to form the samr bicyclic frame. If 3,5-ditrifluoromethylbenzonitrile was employed the corresponding isobornylamide derivative was obtained instead.