Mechanistic insight into thermal 1,3- and 1,5-sulfonyl migrations of N-arenesulfonylphenothiazines and N-arenesulfonylphenoxazines

The substrate scope and mechanistic insight of the thermal-induced 1,3- and 1,5-sulfonyl migration reactions of various sulfonamides have been investigated. The results indicate that both N -arenesulfonylphenothiazines and N -arenesulfonylphenoxazines can undergo 1,3- and 1,5-sulfonyl migrations to...

Full description

Saved in:
Bibliographic Details
Published in:Monatshefte für Chemie 2016-09, Vol.147 (9), p.1637-1649
Main Authors: Wang, Jiandong, Son, Kwon-Il, Xu, Jiaxi
Format: Article
Language:English
Subjects:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The substrate scope and mechanistic insight of the thermal-induced 1,3- and 1,5-sulfonyl migration reactions of various sulfonamides have been investigated. The results indicate that both N -arenesulfonylphenothiazines and N -arenesulfonylphenoxazines can undergo 1,3- and 1,5-sulfonyl migrations to afford the corresponding aryl sulfone derivatives in modest regioselectivities and yields under thermal and neutral conditions. The homolytic cleavage of the sulfonamide bond and intermolecular radical–radical coupling reaction mechanism was proposed for the 1,3- and 1,5-sulfonyl migrations on the basis of intercrossing and competitive capture experiments. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-016-1661-6