Bulletin of the Chemical Society of Japan

Alkylation of benzothiazolines and the Stevens rearrangement of the resulting 2, 3, 3-trisubstituted benzothiazolinium salts.

K Akiba, Y Ohara, N Inamoto

Index: Akiba, Kin-ya; Ohara, Yoshio; Inamoto, Naoki Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 9 p. 2976 - 2983

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Citation Number: 16

Abstract

Alkylation of 2-substituted 3-methyl-or 3-ethylbenzothiazolines with Meerwein reagents gave 2-substituted 3, 3-dialkylbenzothiazolinium tetrafluoroborates (3). The configuration of two alkyl groups on the nitrogen was assigned by NMR spectra and NOE measurement. In the Stevens rearrangement of 3 with lithium diisopropylamide ethyl group showed a much larger migratory aptitude (Et: Me≥ 20: 1) than methyl group irrespective of the configuration of 3, ...