The Journal of Organic Chemistry

Electroreduction of. alpha.,. beta.-unsaturated esters. II. Syntheses of 2, 3-diaryl-5-oxocyclopentane-1-carboxylates by hydrodimerization of cinnamates

LH Klemm, DR Olson

Index: Klemm,L.H.; Olson,D.R. Journal of Organic Chemistry, 1973 , vol. 38, # 19 p. 3390 - 3394

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Citation Number: 31

Abstract

2, 3-Diaryl-5-oxocyclopentane-l-carboxylates (4) were synthesized in yields of 7-60% by electrolytic hydrodimerization of trans cinnamate esters in aphydrous acetonitrile- tetraethylammonium bromide at constant, controlled cathode potential. For cthyl cinnamate as substrate the hydrodimer was found to have the trans-di-phenyl geometry. A mechanism for the formation of 4, involving steps of (a) p, p coupling of oriented anion radicals at the ...

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