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Syntheses of Unsymmetrical Sulfides and Bis(alkylthio)methanes from Diphenylphosphinodithioate Esters

1978/03/01 by Koshiro Goda, Fumito Hanafusa, Naoki Inamoto
Chemistry · #Sulfur-Based Synthesis Techniques #Synthesis and Characterization of Heterocyclic Compounds #Synthesis and Reactivity of Sulfur-Containing Compounds

paper · doi:10.1246/bcsj.51.818

crossref issued 1978/03/01 · crossref published 1978/03/01 · crossref published-print 1978/03/01 · openalex publication_date 1978/03/01 · crossref published-online 2006/04/19 · crossref created 2006/07/20 · crossref deposited 2024/01/17 · openalex created_date 2025/10/10 · crossref indexed 2026/07/30 · openalex updated_date 2026/07/30

Abstract

Abstract Unsymmetrical sulfides were prepared by the reactions of diphenylphosphinodithioate esters with organolithiums in tetrahydrofuran (THF) at −78 °C or at room temperature in fairly good or excellent yields. Similarly, methylene bis(diphenylphosphinodithioate) gave bis(alkylthio)methanes by reactions with organolithiums in good yields. The use of bad-smelling thiols is avoided and the phosphorus part can be recycled after sulfurization and esterification. Allyl diphenylphosphinodithioate gave allylbenzene via SN2(C) reaction upon treatment with phenylmagnesium bromide in refluxing THF.

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