A berzelius reagent, phosphorus decasulfide (P4S10), in organic syntheses

Turan Ozturk*, Erdal Ertas, Olcay Mert

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

168 Citations (Scopus)

Abstract

Berzelius has synthesized P4S10 by reaction of white phosphorus and sulfur. P4S10 has been used widely in organic syntheses for a wide range of purposes such as a thionating agent of organic compounds and for the syntheses of various heterocycles, including thiophenes, thiazines, thiazoles, thiazolines, imidazolines, pyrimidines, imides, dithiazoles, thiadiazoles, and dithiins. The usual method of thionation using P4S10 has been conducted in refluxing solvents such as benzene, toluene, dioxane, xylene, THF, pyridine, acetonitrile, and CS 2. The reaction of α, β-unsaturated ketone with P 4S10 in CS2 gives an intramolecular Diels-Alder reaction to yield the cyclo adduct possibly through the thione intermediate. Trithiapentalenes has been obtained from 1,3,5-triketones and the treatment of the triketones with P4S10 in refluxing toluene yielded the trithiapentalenes.

Original languageEnglish
Pages (from-to)3419-3478
Number of pages60
JournalChemical Reviews
Volume110
Issue number6
DOIs
Publication statusPublished - 9 Jun 2010

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