NEW REARRANGEMENTS OF THE CARYOPHYLLENE SKELETON: THE DINITROPHENYLHYDRAZONES FROM CARYOPHYLLENE OXIDE

Abstract

Caryophyllene oxide (I) and dihydrocaryophyllene oxide (II) have been found to give 2,4-dinitrophenylhydrazones. Structures IV, V, and VII are assigned to three of these compounds on the basis of nuclear magnetic resonance data, other spectral and chemical data, and mechanistic considerations. Structure VII is the product of a new cyclization–rearrangement of the caryophyllene system. The dinitrophenylhydrazone previously obtained from isocaryophyllene oxide-a (III) is probably identical with VII. Three other new derivatives of caryophyllene are described, one of which (VI) is an intermediate in the conversion of I to VII.