Synthesis of 2,2-dialkyl-1-aminocyclopropanecarboxylic acids from .alpha.-chloro ketimines

Abstract

2,2-Dialkyl-1-aminocyclopropanecarboxylic acids, abbreviated as 2,2-dialkyl Acc's, are potential plant growth regulators which were synthesized by ring closure of α-chloro imines. The synthetic scheme leading to these Acc analogues entails a newly developed regiospecific synthesis of tertiary α-chloro ketimines, the trapping with cyanide of a transient Favorskii derived cyclopropylideneamine, and the hydrolytic conversion of 1-(N-tert-butylamino)-2,2-dialkylcyclopropanecarbonitriles into the title compounds