Reactions of ketone hydrazones and .BETA.-keto enamines with disulfur dichloride. New synthesis of thioketones and 5H-1,2,3-dithiazoles.

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概要

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• Ketone hydrazones react with disulfur dichloride in the presence of triethylamine to afford thioketones in good yields. The reaction mechanism involving <I>N</I>-thiosulfinylamine (R<SUB>2</SUB>C=N–N=S=S) and <I>S</I>-thioxothioketone (R<SUB>2</SUB>C=S=S) is proposed. The formation of <I>t</I>-butyl and di-1-adamantyl thioketones even at low temperatures has been interpreted as steric congestion alone being not enough to stabilize the corresponding <I>S</I>-thioxothioketones. The reaction of β-ketoenamines with disulfur dichloride gives 5<I>H</I>-1,2,3-dithiazoles <I>via</I> intramolecular cyclization of intermediary <I>N</I>-thiosulfinylamines.

• 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

• Inoue Kaoru

  Department Of Anatomy Hokkaido University School Of Medicine

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