Ritter Reaction with Cyclopropyl Ketones and Cyclopropyl Alcohols: Synthesis of N-Actyl- γ-Keto and N-Acyl Hohoallyl Amines

Abstract

A variety of conjugated cyclopropyl ketones and cyclopropylcarbinyl alcohols were reacted with two nitriles viz. CH₃ CN and CH₂[dbnd]CH-CN in presence of cone. H₂ SO₄. It was found that with appropriate substitutions cyclopropyl ketones gave N-Acyl-γ-keto amines whereas cyclopropylcarbinyl alcohols gave the corresponding N-Acyl homoallylic amines in reasonably good yields. The olefins obtained had E-stereo-chemistry. With bicyclic cyclopropylcarbinyl alcohols the ring expanded products were formed. A plausible rationale is provided to account for these observations