Reaction of N-tert-butyl-2-benzothiazolesulphenamide with acetic anhydridein the presence of acids II. Spectral studies

The reaction of N-tert-butyl-2-benzothiazolesulphenamide with acetic anhydr ide catalyzed by acetic acid in a nonpolar solvent has been studied by NMR, GC-MS and EPR techniques. In the catalytic process homolytic decomposition of N-tert-butyl-2-benzothiazolesulphenamid prevails over the heterolytic p athway which is typical for uncatalyzed reaction. Besides the typical produ cts formed during the uncatalyzed reaction, in the acid catalyzed process p roducts formed by recombination of radicals were confirmed by C-13 NMR and mass spectroscopy. In the formation of TBbisBS by homolytic pathway N,N'-di alkylhydrazine radicals and RNH. radicals, produced by decomposition of N,N '-dialkylhydrazine, play probably an important role. (C) 2001 Elsevier Scie nce B.V. All rights reserved.