The Collision-Induced Dissociations of Deprotonated Isopropyl and t-Butyl Ketones. Some Unusual Alkyl Migrations

Abstract

Rearrangement reactions involving hydride and methyl anion migrations are observed when certain enolate ions derived from isopropyl and t- butyl ketones are subjected to collisional activation. For example (i) -CH2CO-i-C3H7 → -(CH2CHO)+C3H6 and (ii) -CH2CO-t-C4H9 → -(CH2COCH3)+C3H6The mechanisms of these and related reactions have been investigated by denterium labelling and product ion studies.