Syntheses of Unsymmetrical Sulfides and Bis(alkylthio)methanes from Diphenylphosphinodithioate Esters
- 1 March 1978
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 51 (3) , 818-820
- https://doi.org/10.1246/bcsj.51.818
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.This publication has 3 references indexed in Scilit:
- Reactions of Alkyl Diphenylphosphinates and Related Thio Esters with Some Nucleophiles. SN2 (S) Reaction and Wittig Type RearrangementBulletin of the Chemical Society of Japan, 1978
- Allylic Rearrangements. XXVI. The Reaction of Butenyl Mesitoates and Chlorides with Phenylmagnesium BromideJournal of the American Chemical Society, 1949
- The Yields of Some Organolithium Compounds by the Improved ProcedureJournal of the American Chemical Society, 1933