Studies on the Reduction of Terpenes with Sodium in Aqueous Ammonia

Part VIII. On the Reduction of (-)-Isomenthone

Abstract

In the reduction of (-)-isomenthone with sodium in aqueous ammonia, it was found that the reduction product gives a mixture consisting of 75.5% of (-)-isomenthol (a, e, e), 9.5% of (+)-menthol (e, e, e) and 8.6% of (-)-neoisomenthol (a, a, e). From this fact, it might be concluded that this reduction is stereospecific for isomenthone and is mechanistically different from reduction with sodium and alcohol.