Characterizations In Studying The Effect Of Acid Reagent Of The Rearrangement Reaction Of Camphoroxime Producing Different Ratios Of The αβ-Campholene Nitriles

Abstract

There are two major steps in the synthesis of pleasant fragrant α- and β- campholene nitriles from camphor. The first is the reaction of hydroxylamine with camphor to give the camphoroxime, which rearranges in the presence of acid during the second step to give eitherα- or β- or both αβ- campholene nitriles. The nature of the acid determines the type of isomer(s) formed and the amount of each isomer in the product. This paper reports the rearrangement products of camphoroxime using HI, PCl5, HNO3 and CH3COOH acids, which are rarely used in literature. Also H2SO4, HNO3, HI, PCl5 and H3PO4 were found to give very high yields (79% and above) of the fragrant campholene nitriles, while organic acid catalysts gave campholene nitriles in very low yields (<5%).

IFE Journal of Science Vol. 9 (2) 2007 pp. 231-240