SUCCINOYLATION OF -SULFONYLCABBANIONS: SIMPLE SYNTHESES OF SYM-1,4-DIKETONES

MANAT POHMAKOTR and DUSANEE VANICHPITMONANAN

ABSTRACT: Reactions of -adilithio carbanions derived from (phenylsulfonyl)alkanes with dimethyl succinate followed by reductive cleaVage with aluminum amalgam in aqueous tetrahydrofuran provide convenient syntheses of various sym-1,4-diketones. The analogous reactions with succinic anhydride lead to moderate yields of -keto acids.

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Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand

Recieved 20 May 1983