ELECTRONIC EFFECTS ON THE REGIOSELECTIVITY IN THE REACTIONS OF THIOALLYLIC ANIONS WITH CARBONYL COMPOUNDS

Abstract

In the reactions of lithium salts of allylic N, N-dimethyldithiocarbamates with p-substituted aromatic aldehydes and ketones, the α-selectivity increases as the substituent of the phenyl ring becomes more electron-attractive. The regioselectivity also depends upon the substitution pattern of the allylic moiety. The Hard and Soft Acid and Base (HSAB) approach was used to rationalize the results.