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
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1836-1838
- https://doi.org/10.1039/p19720001836
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.Keywords
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