Cyclohexenone derivatives. Part VI. C-3 and C-1 alkylation of Hagemann's ester (ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate) with alkyl halides and Michael acceptors

Abstract

Reactions of Hagemann's ester with alkyl halides and Michael acceptors under basic conditions have been studied; the ratios of C-1 to C-3 alkylated products have been determined by g.l.c. and n.m.r. spectroscopy. The higher yield of C-1 alkyl esters from Michael reactions in comparison with simple alkylations has been rationalised on the basis of steric and electronic factors in the transition states.