Central Nervous System Active Compounds. XVII. Some Reactions of 6-Chloro-4,4-dimethyl-1,3,4,5-tetrahydro-2H-azepin-2-one and Its Dechlorinated Derivative

MR Hatswell, RH Prager and AD Ward

Abstract

The vinyl chloride group of the title compound can be reduced to the enamide by using sodium metal. The enamide reacts with diborane or mercuric acetate to place a functional group at C7. The vinyl chloride is stable to hydrolysis under a variety of mild conditions but reacts with alkoxides under reflux to form a 6,7-dialkoxy derivative. A small amount of a dimer was obtained from the reaction of a mixture of unsaturated chlorocaprolactams with hydroxide.

Australian Journal of Chemistry 46(1) 135 - 141 (1993) doi:10.1071/CH9930135