Vinylcyclopropyl anion: structure, reactivity, thermodynamic properties, and an unusual rearrangement

Abstract

Vinylcyclopropane (1) is deprotonated in the gas phase by NH 2 - or Me 2 N - to afford its conjugate base (1a). Vinylcyclopropyl anion is quite basic (ΔH acid (1)=394±3 kcal mol -1 ), has a relatively small electron binding energy (12±5 kcal mol -1 ), and reacts with a variety of reagents including N 2 O, CS 2 , COS, O 2 , and SO 2