Conversion of sterically hindered phenols into the corresponding N,N-dimethylarenesulfonamides via the Newman-Kwart rearrangement

✍ Scribed by Anno Wagenaar; Jan B. F. N. Engberts

• Book ID: 104588407
• Publisher: Elsevier Science
• Year: 2010
• Tongue: English
• Weight: 377 KB
• Volume: 101
• Category: Article
• ISSN: 0165-0513
• DOI: 10.1002/recl.19821010304

✦ Synopsis

Abstract

The 2‐alkyl‐ and 2,6‐dialkylbenzenesulfonyl chlorides 5a‐f were obtained in high yield by chlorination of the correspondingly substituted S‐aryl N,N‐dialkylthiocarbamates 4a‐g. These precursors have been synthesized via the Newman‐Kwart rearrangement of the corresponding O‐aryl N,N‐dialkylthiocarbamates 3a‐g, which are easily prepared from the sterically hindered phenols 1a‐g. The sulfonyl chlorides 5a‐f are readily transformed into the desired 2‐alkyl‐ and 2,6‐dialkyl‐N,N‐dimethylbenzenesulfonamides 6a‐f.