Reactions of Terpene Alcohols and Diols with Chlorine Dioxide in Dimethylformamide

摘要

The system chlorine dioxide-dimethylformamide in combination with or without a catalytic amount of MoCl5, CeCl3, ZrOCl2, or VO(acac)(2) induces oxidative chlorination of a number of bicyclic terpene alcohols and vicinal diols. 2 alpha-Chloropinan-3-one, 3 alpha-chloro-10 beta-pinan-4-one, 5 alpha-chloro-3 alpha-hydroxycaran-4-one, 5 beta-chloro-3 beta-hydroxycaran-4-one, and 4 alpha-chloro-2 alpha-hydroxypinan-3-one were thus synthesized in good preparative yields.