Diethyl, 2,5-dimethylcyclohept-4-ene-1.1-dicarboxylate has been synthesised from ethyl 3-methyl-2-oxocyclopentane-1-carboxylate via a bicyclic tosyloxy-ketone intermediate. Only one of the ester functions is hydrolysed by alkali and the resulting half-ester has been converted into the title ketone. A new fragmentation reaction of an axial tosyloxy-ketone is reported.
H. L. Brown, G. L. Buchanan and J. O'Donnell, J. Chem. Soc., Perkin Trans. 1, 1979, 1740 DOI: 10.1039/P19790001740
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