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

ISSN: 1570-1786
E-ISSN: 1875-6255

Competitive Deprotonation in Vicinal O=SCH2CH2P=O Moieties
Authors: Nina K. Gusarova¹, Nataliya A. Chernysheva², Svetlana N. Arbuzova³, Maria V. Bogdanova⁴, Svetlana F. Malysheva⁵, Nataliya A. Belogorlova⁶, Igor A. Ushakov⁷, Nadezhda M. Vitkovskaya⁸, Vladimir B. Kobychev⁹ and Boris A. Trofimov¹⁰
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¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ² A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ³ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ⁴ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ⁵ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ⁶ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ⁷ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ⁸ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ⁹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia. ¹⁰ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033 Irkutsk, Russia.
Source: Letters in Organic Chemistry, Volume 3, Issue 9, Sep 2006, p. 720 - 722
DOI: https://doi.org/10.2174/157017806778700097
- Available online: 01 Sep 2006

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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2006-09-01

2025-09-16

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Article Type: Research Article

Keyword(s): Carbanions; diphenyl(vinyl)phosphine oxide; diphenyl[2-(phenylsulfinyl)ethyl]phosphine oxide; quantum chemical calculations; sodium amide

Competitive Deprotonation in Vicinal O=SCH2CH2P=O Moieties

Abstract

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