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REACTIONS OF CHLOROMETHYL PHENYL SULFONE CARBANION WITH NITROBENZOPHENONES. THE VICARIOUS SUBSTITUTION OF HYDROGEN Versus THE DARZENS CONDENSATION

1984; Oxford University Press; Volume: 13; Issue: 10 Linguagem: Inglês

10.1246/cl.1984.1619

1348-0715

Mieczysław Ma̧kosza, J. GOLINSKI, Janusz Baran, D. Dziewonska‐Baran,

Organic and Inorganic Chemical Reactions

Abstract Carbanion of chloromethyl phenyl sulfone replaces hydrogen atoms o′- and p- to the nitro group in o-nitrobenzophenone, whereas with p-nitrobenzophenone it enters the Darzens condensation followed by rearrangement and decarbonylation. Reaction course with m-nitrobenzophenone depends on the conditions (base concetration). When an excess of a base is present the vicarious substitution of hydrogen takes place whereas low concentration of a base favours the Darzens condensation.