Competitive Deprotonation in Vicinal O=SCH2CH2P=O Moieties

Authors: Gusarova, Nina K.; Chernysheva, Nataliya A.; Arbuzova, Svetlana N.; Maria V. Bogdanova,; Malysheva, Svetlana F.; Belogorlova, Nataliya A.; Ushakov, Igor A.; Vitkovskaya, Nadezhda M.; Kobychev, Vladimir B.; Trofimov, Boris A.

Source: Letters in Organic Chemistry, Volume 3, Number 9, September 2006 , pp. 720-722(3)

Publisher: Bentham Science Publishers

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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

Document Type: Research article

Affiliations: 1: A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia.

Publication date: 2006-09-01

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