A convenient synthesis of the flavor and scent material (±)-γ-(Z)-6-dodecenolactone and some analogs via N-chloroamide thermolysis

Abstract

N-Chloro-N-propyl-threo-6,7-dibromododecanamide, prepared by the successive bromination and N-chlorination of N-propyl-(Z)-6-dodecenamide, was subjected to thermolytic homolysis in aqueous dioxane to yield a mixture of products from which, after zinc debromination, γ-6-(Z)-dodecenolactone was isolated. Some analogs of this lactone were similarly prepared.