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Communication | Special issue | Vol 11, No. 1, 1978, pp.231-234
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0231
Migratory Aptitude of the Ethyl and the Methyl Groups during Stevens Rearrangement of N,N-Dialkyl-2-arylbenzothiazolinium Salts

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

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

Abstract

Stereochemical relation between the migrating group on the ammonium nitrogen and the carbanion was investigated on Stevens rearrangement of N,N-dialkylbenzothiazolinium salts to show large migratory aptitude of the ethyl against the methyl group (Et: Me > 20:1), where cyclic ammonium ylide with planar π-type carbanion was proposed to be the intermediate.