Replacement of the carbonyl oxygen of hydroxy ketones by methylene and 1, 1-ethano groups by reaction with the Simmons-Smith reagent

IT Harrison, RJ Rawson, P Turnbull…

Index: Harrison,I.T. et al. Journal of Organic Chemistry, 1971 , vol. 36, # 23 p. 3515 - 3517

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Citation Number: 20

Abstract

In a previous communication we reported2 the unexpected formation of methylene and ethano derivatives 2 and 3 by reaction of 17p-acetoxy-1 lp-hydroxyestr-5 (10)-en-3-one (1) with a reagent derived from methylene iodide and zinc-copper couple (Simmons-Smith reagent). Further work has shown that the reaction is not limited to hydroxy ketones; for example, 50-androstan-3-one (4) was converted into a mixture of 3, 3-methylene-5a- ...

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