Thiophosphoryl bromide: a new reagent for the reduction of sulfoxides to sulfides
β Scribed by I.W.J. Still; J.N. Reed; K. Turnbull
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 222 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Thiophosphoryl bromide (PSBrS) has been found to be a mild,effective reagent for the reduction of sulfoxides of widely differing structural types to the corresponding sulfides. * A number of new procedures for the reduction of sulfoxides have recently been reportedIm6 and at least two excellent reviews of this synthetic conversion have also appeared recently. 798 We ourselves have recently described the use of phosphorus pentasulfide as a versatile reagent not only for reducing sulfoxides but also for the reduction of related classes of compounds, such as sulfimides (sulfilimines) and selenoxides. 9 We now wish to report the successful application of a simple new reagent for the sulfoxide to sulfide conversion, namely, thiophosphoryl bromide (PSBrS)." To our knowledge, this represents the first general applicaLion of thiophosphoryl bromide as a reagent in organic synthesis. As the results in the Table indicate, thiophosphoryl bromide has proved to be, in several ways, a superior reagent to phosphorus pentasulfide for the reduction of sulfoxides. It is readily available commercially, or it may conveniently be synthesized from red phosphorus, bromine and phosphorus pentasulfide, in 67% yield. 11 The reagent, although a low-melting solid,
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