Synthesis and properties of o-thioquinone methides having ketene aminal, ketene acetal, ketene monothioacetal, or ketene dithioacetal group.

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概要

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• Reaction of 1,2-benzodithiole-3-thione with <I>N</I>,<I>N</I>′-dialkyl-1,2-ethanedianiine afforded <I>o</I>-thioquinone methides with a ketene aminal group (<B>6</B>) in high yields. Two similar thionaphthoquinone methides were also prepared. <I>o</I>-Thioquinone methide derived from <I>N</I>,<I>N</I>′-dimethyl-<I>o</I>-phenylenediamine was prepared from 3-chloro-1,2-benzodithiol-3-ylium chloride (<B>10</B>). These compounds were found to exist as a monomer of a considerable betaine nature. Reactions of <B>6a</B> (<I>N</I>,<I>N</I>′-dimethyl derivative) with dimethyl acetylenedicarboxylate and dibenzoylacetylene led to [4+2] adducts. <I>o</I>-Thioquinone methides with a ketene acetal group were obtained from desulfurization of spiro[1,3-benzodioxole-2,3′-[1,2]benzodithiole] with trimethyl phosphite, which are equilibrated with two kinds of aggregates; one is a dimer and the other is a trimer or a higher oligomer. Reactions of <B>10</B> with <I>o</I>-mercaptophenol and 1,2-benzenedithiols gave spiro[1,2-benzodithiole-3,2′-[1,3]benzoxathiole] (<B>29</B>) and spiro[1,2-benzodithiole-3,2′-[1,3]benzodithiole] (<B>39</B> and <B>40</B>), respectively. <I>o</I>-Thioquinone methide with a ketene monothioacetal group (<B>30</B>) was prepared by desulfurization of <B>29</B>. The violet compound <B>30</B> is equilibrated with a colorless dimer. This <I>o</I>-thioquinone methide reacted with olefins and an acetylene having electron-withdrawing groups to give 1,4-cycloaddition products. Similar desulfurization of <B>39</B> and <B>40</B> gave <I>o</I>-thioquinone methides with dithioacetal group. Their properties were very similar to those of <I>o</I>-thioquinone methides with dithioacetal group prepared by the photoreaction of <B>2</B> with olefins.

• 公益社団法人 日本化学会の論文

著者

• Kang Kyung-tae

  Department Of Chemistry And Chemistry Institute For Functional Materials Pusan National University

• 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

• Kang Kyung-Tae

  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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