On the reaction of bis(phosphothioyl)disul-fanes with hydroxamic acids, part I: Ionic versus radical reaction pathways
✍ Scribed by Witold Przychodzeń; Jarosław Chojnacki
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 357 KB
- Volume
- 19
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20423
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✦ Synopsis
Abstract
Among sodium N‐alkyl‐4‐chlorobenzo‐hydroxamates treated with bis(phosphothioyl)disul‐fanes >P(S)SSP(S)< (where >P(S) is phosphorothioyl, phosphonothioyl, and phosphinothioyl), only the N‐methyl one yields quantitatively the respective O‐phosphothioyl derivatives exhibiting complete inversion of configuration at phosphorus in a reaction whose products are inert toward dithiophosphate arising in the reaction. For branched N‐alkyl benzohydroxamates, products of a SET process predominated. The mechanism of the title reaction is discussed. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:271–282, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20423