Cyclohexenone Derivatives : Part V. Further Studies on Alkylation of Hagemann's Ester

In continuation of previous studies, Hagemann's ester has been alkylated with a variety of alkyl halides. The products, in each case a mixture of C3- and C1-substituted esters, are analysed by N.M.R. spectroscopy, the ratio of the two being determined by the relative areas of the vinyl proton at C3 and allylic proton at C1. Contrary to previously accepted view, the C1-alkylation of Hagemann's ester is found to be a general phenomenon and occurs to the extent of 2-51% depending on the nature of alkylatirg agent and the kind of base used. Hagemann's ester has also been alkylated with di-, tri-, and tetra-methylene dihalides giving mainly spirocompounds as a result of 3, 3-dialkylation