Chemistry of N-thiosulfinylanilines. I. Reactions of sterically hindered anilines with sulfur chlorides. Preparation of N-thiosulfinylanilines.

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概要

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• Reaction of 2,4-di-<I>t</I>-butyl-6-methylaniline (<B>3</B>) with disulfur dichloride afforded 2,4-di-<I>t</I>-butyl-6-methyl-<I>N</I>-thiosulfinylaniline (<B>4</B>) as a stable compound in 80% yield. Reaction of 2,4,6-tri-<I>t</I>-butylaniline (<B>1</B>) with disulfur dichloride gave in 70% yield 2,4,6-tri-<I>t</I>-butyl-7,8-dithia-9-azabicyclo[4.3.0]nona-2,4,9-triene, which in solution, exists as a tautomeric mixture with 2,4,6-tri-<I>t</I>-butyl-<I>N</I>-thiosulnnylaniline (<B>2b</B>) as a minor component. In the reactions with 2,4-di-<I>t</I>-butyl-6-isopropyl- or 2,4,6-trimethylaniline, <I>N</I>-thiosulfinylanilines obtained were unstable at ambient temperature. Aniline <B>1</B> reacted with sulfur dichloride to give <B>2</B> and the corresponding sulfur diimide and <I>N</I>-sulfinylaniline. The reaction of <B>4</B> with the dichloride afforded <B>4</B> and the corresponding sulfur diimide.

• 公益社団法人 日本化学会の論文

著者

• Inamoto Naoki

  Department Of Chemistry Graduate School Of Science The University Of Tokyo

• Okazaki Renji

  Department Of Chemical And Biological Sciences Faculty Of Science Japan Women's University

• Inagaki Yoshio

  Department of Chemistry, Faculty of Science, The University of Tokyo

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