Chemistry of N-thiosulfinylanilines. IV. Reactions of N-thiosulfinylanilines with electrophilic reagents.

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概要

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• Reaction of 2,4-di-<I>t</I>-butyl-6-methyl-<I>N</I>-thiosulfinylaniline (<B>1</B>) with <I>m</I>-chloroperbenzoic acid (MCPBA) afforded the corresponding aniline and <I>N</I>-sulfinylaniline. Reaction of MCPBA with 2,4,6-tri-<I>t</I>-butyl-7,8-dithia-9-azabicyclo[4.3.0]nona-2,4,9-triene equilibrated with 2,4,6-tri-<I>t</I>-butyl-<I>N</I>-thiosulflnylaniline gave 2,4,<I>r</I>-6-tri-<I>t</I>-butyl-7,8-dithia-9-azabicyclo[4.3.0]nona-2,4,9-triene <I>t</I>-7-oxide (<B>12</B>), 4,6-di-<I>t</I>-butyl-3<I>H</I>-1,2,3-benzodithiazole 2-oxide (<B>13</B>), and 2,4,6-tri-<I>t</I>-butyl-<I>N</I>-sulfinylaniline (<B>14</B>). The oxide <B>13</B> was considered to be produced <I>via</I> a primary product 2,4,<I>r</I>-6-tri-<I>t</I>-butyl-7,8-dithia-9-azabicyclo[4.3.0]nona-2,4,9-triene <I>t</I>-8-oxide which was found to be unstable above −30 °C. Thermolysis of <B>12</B> affording <B>13</B>, <B>14</B>, and 2,4,6-tri-<I>t</I>-butylaniline demonstrated oxygen or sulfur migration in the thiosulfinate type compound. Bromine reacted with <B>1</B> to give bis(2,4-di-<I>t</I>-butyl-6-methylphenyl)sulfur diimide probably <I>via</I> a thionitroso intermediate. Neither trimethyloxonium tetrafluoroborate nor trimethylsilyl chloride reacted with <B>1</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

• Inamoto Naoki

  Department of Chemistry and Research Centre for Spectrochemistry, Faculty of Science, The University of Tokyo

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