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Communication | Special issue | Vol 13, No. 1, 1979, pp.289-292
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0289
Selective Migration of the 0-Alkylthiophenyl Group in Stevens Rearrangement

Yoshio Ohara, Kin-ya Akiba,* and Naoki Inamoto

*Department of Chemistry, Faculty of Science, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033

Abstract

2-Aryl-3,3-dimethylbenzothiazolinium tetrafluoroborate (1) suffers nucleophilic attack at the ring sulfur atom by butyllithium to afford the ring-opened ammonium ylide (A), which collapses to the radical pair (B) to give unusual Stevens rearrangement product (2) as a major product, where the o-alkylthiophenyl group migrated selectively in preference to the methyl group.