Malonate anion induced Favorskii-type rearrangement. Reaction of cyclic. alpha.-halo ketones with sodiomalonates

…, E Amano, A Kawabata, A Takeda

Index: Sakai, Takashi; Amano, Eiichiro; Kawabata, Akifumi; Takeda, Akira Journal of Organic Chemistry, 1980 , vol. 45, # 1 p. 43 - 47

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Citation Number: 19

Abstract

The reaction of 2-chlorocyclohexanone (lb) with ethyl sodiomalonate in benzene at 0-25" C gave 6-[bis-(ethoxycarbonyl) methyl] bicyclo [3.1. 0] hexan-6-ol (4c), the Favorskii-type intermediate, in 49% yield, in place of the substitution product ethyl C-(2-oxocyclohexyl) malonate (3). Derivatives of bicyclo [4.1. 0] heptan-7-ol (4a, b) and those of bicyclo [3. l. 0] hexan-6-01 (4d, e) were also obtained in good yields by similar means. Compound 4c ...