The Journal of Organic Chemistry

Radical addition to carbonyl carbon promoted by aqueous titanium trichloride: stereoselective synthesis of. alpha.,. beta.-dihydroxy ketones

A Clerici, O Porta

Index: Clerici, Angelo; Porta, Ombretta Journal of Organic Chemistry, 1989 , vol. 54, # 16 p. 3872 - 3878

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Citation Number: 32

Abstract

(Table I). Benzil (la) and 1-phenyl-1, Zpropanedione (IC) were reduced to the corresponding a-hydroxy ketones, probably through disproportionation of the intermediate ketyl radical^;^^^ phenylglyoxal (lb) afforded the dimer 1, 4-dipheny1-2, 3-dihydroxy-1, 4-butanedione (60 90) and a-hydroxyacetophenone (30%). From the data in Table I it emerges that these reductions are chemoselective: reduction of lb occurs solely at the aldehydic function, ...