Alkylation of 2-oxy-substituted 1-sulfonylallyl and 1-sulfonylvinyl anions. New routes to functionalized carbocycles and dihydrofurans

…, SW McCombie, BB Shankar, AK Ganguly

Index: Padwa, Albert; Bullock, William H.; Dyszlewski, Andrew D.; McCombie, S. W.; Shankar, B. B.; Ganguly, A. K. Journal of Organic Chemistry, 1991 , vol. 56, # 11 p. 3556 - 3564

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Citation Number: 23

Abstract

Alkylation of the anion derived from 2-phenoxy-3-(phenylsulfonyl)-l-propene proceeds a to the phenylsulfonyl group and affords cyclic products from 1, wdihalides. Reaction of the monoalkylated producte, in which a suitably positioned olefinic or acetylenic unit is present, with sodium benzenesulfinate-acetic acid gives functionalized acetylcyclopentenes and cyclohexenes via CC bond formation from the allyl cation-sulfinate ion pair. In the vinyl ...

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