Chemistry of N-thiosulfinylanilines. V. Reactions of N-thiosulfinylanilines with nucleophilic reagents.

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概要

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• 2,4-Di-<I>t</I>-butyl-6-methyl-<I>N</I>-(thiosulfinyl)aniline (<B>1</B>) gave 2,4-di-<I>t</I>-butyl-6-methylaniline in the reactions with such reagents as alkylamines, thiourea, butyllithium, alkylmagnesium halides, 1-(1-pyrrolidinyl)cyclopentene, and hydrogen sulfide. Triphenylphosphine reacted with <B>1</B> to give (2,4-di-<I>t</I>-butyl-6-methylphenylimino)triphenylphosphorane and bis(2,4-di-<I>t</I>-butyl-6-methylphenyl)sulfur diimide. Reaction of triphenylphosphine with 2,4,6-tri-<I>t</I>-butyl-7,8-dithia-9-azabicyclo[4.3.0]nona-2,4,9-triene afforded 2,4,6-tri-<I>t</I>-butylaniline, bis(2,4,6-tri-<I>t</I>-butylphenyl)sulfur diimide, and 2,4,6-tri-<I>t</I>-butyl-<I>N</I>-sulfinylaniline (<B>7</B>). The sulfur diimide was considered to be formed <I>via</I> intermediary 2,4,6-tri-<I>t</I>-butylthionitrosobenzene, which was trapped by oxygen to give the <I>N</I>-sulfinyl derivative <B>7</B>.

• 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

• Hosogai Takeo

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

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