Abstract
Diphenyl[2-(phenylsulfinyl)ethyl]phosphine oxide readily accessible from diphenylphosphine oxide and phenyl vinyl sulfoxide reacts with sodium amide to form diphenyl(vinyl)phosphine oxide in good yield. The reaction involves generation of phosphoryl-stabilized carbanions which further eliminate benzene sulfenate anions. The preferred formation of phosphoryl-stabilized carbanions in the vicinal O=SCH2CH2P=O moiety is supported by quantum chemical calculations. Keywords: Carbanions, diphenyl[2-(phenylsulfinyl)ethyl]phosphine oxide, sodium amide, diphenyl(vinyl)phosphine oxide, quantum chemical calculations
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