Competitive Deprotonation in Vicinal O=SCH2CH2P=O Moieties

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

doi:10.2174/157017806778700097

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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Letters in Organic Chemistry

Title: Competitive Deprotonation in Vicinal O=SCH2CH2P=O Moieties

Volume: 3 Issue: 9

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

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Keywords: Carbanions, diphenyl[2-(phenylsulfinyl)ethyl]phosphine oxide, sodium amide, diphenyl(vinyl)phosphine oxide, quantum chemical calculations

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.

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Gusarova K. Nina, Chernysheva A. Nataliya, Arbuzova N. Svetlana, Maria V. Bogdanova , Malysheva F. Svetlana, Belogorlova A. Nataliya, Ushakov A. Igor, Vitkovskaya M. Nadezhda, Kobychev B. Vladimir and Trofimov A. Boris, Competitive Deprotonation in Vicinal O=SCH2CH2P=O Moieties, Letters in Organic Chemistry 2006; 3 (9) . https://dx.doi.org/10.2174/157017806778700097