Synlett

Synthesis of Benzylidenecyclopropanes from γ-Halopropyl Pentachlorophenyl Sulfones Using a Julia-Kocienski Olefination

M Mąkosza, R Bujok

Index: Makosza, Mieczyslaw; Bujok, Robert Synlett, 2008 , # 4 p. 586 - 588

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Citation Number: 5

Abstract

In the course of our studies on the reaction of γ-halocarbanions, [8] we have observed that carbanion of 3-chloropropyl pentachlorophenyl sulfone in the reaction with aromatic aldehydes gave 1-aryl-4-chloro-1-butene products of Julia-Kocienski olefination, instead of expected 2-aryl-3-pentachlorophenylsulfonyl tetrahydrofuranes. [9] Obviously, in the initial aldol-type adducts oxygen anion adds to the electron-deficient aromatic ring, so the Smiles rearrangement ...