Lawesson's reagent for direct thionation of hydroxamic acids: Substituent effects on LR reactivity
✍ Scribed by Witold Przychodzeń
- Book ID
- 102230992
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 154 KB
- Volume
- 17
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20259
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✦ Synopsis
Abstract
To explore the generality and scope of direct thionation of hydroxamic acids (HAs), the reaction of various structurally diverse HAs with Lawesson's reagent was investigated. The yield of thiohydroxamic acid (THAs) is poor when HAs possess bulky acyl and/or N‐substituents, acidic α‐hydrogen atoms, or an N‐phenyl ring. THAs yields were correlated with Brown sigma parameter. The relative rates of two subsequent processes k and k were also measured. Correlation was also found for methine proton chemical shifts of N‐isopropyl benzothiohydroxamic acids. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:676–684, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20259