On the reaction of bis(phosphothioyl)disul-fanes with hydroxamic acids, part I: Ionic versus radical reaction pathways

Corresponding Author

Witold Przychodzeń

[email protected]

Faculty of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80952 Gdańsk, Poland

Faculty of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80952 Gdańsk, PolandSearch for more papers by this author

Jarosław Chojnacki,

Jarosław Chojnacki

Faculty of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80952 Gdańsk, Poland

Search for more papers by this author

Witold Przychodzeń,

Corresponding Author

Witold Przychodzeń

[email protected]

Faculty of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80952 Gdańsk, Poland

Faculty of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80952 Gdańsk, PolandSearch for more papers by this author

Jarosław Chojnacki,

Jarosław Chojnacki

Faculty of Chemistry, Gdańsk University of Technology, Narutowicza 11/12, 80952 Gdańsk, Poland

Search for more papers by this author

First published: 03 April 2008

https://doi.org/10.1002/hc.20423

Citations: 10

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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

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On the reaction of bis(phosphothioyl)disul-fanes with hydroxamic acids, part I: Ionic versus radical reaction pathways

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On the reaction of bis(phosphothioyl)disul-fanes with hydroxamic acids, part I: Ionic versus radical reaction pathways

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