Preparation and reactions of 5-aryl-1,4,2-dithiazolium salts.

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概要

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• <I>S</I>-Thioaroylsulfenamides (ArCSSNH<SUB>2</SUB>), formed by reaction of ArCSS<SUP>−</SUP>Na<SUP>+</SUP> with hydroxylamine-<I>O</I>-sulfonic acid, were aroylated or acylated to give <I>N</I>-aroyl- or <I>N</I>-acyl-<I>S</I>-thioaroylsulfenamides, respectively, which were then cyclized with dehydration to afford 3-substituted 5-aryl-1,4,2-dithiazolium salts. The behavior of 3,5-diphenyl-1,4,2-dithiazolium perchlorate toward nucleophiles such as active methylene and amino compounds was studied systematically. The reaction can be classified into two cases depending on fission modes of initial adducts, i.e., ring opening–ring closure reaction (Path B) and fragmentation of dithiazole ring (Path C), and in some cases the initial adducts were isolated.

• 公益社団法人 日本化学会の論文

著者

• Shibuya Isao

  National Institute Of Advanced Industrial Science And Technology(aist) Tsukuba Central 5

• TAGUCHI Yoichi

  National Institute of Advanced Industrial Science and Technology (AIST)

• YASUMOTO Masahiko

  National Chemical Laboratory for Industry

• Tsuchiya Tohru

  National Chemical Laboratory for Industry

• Yonemoto Katsumi

  National Chemical Laboratory for Industry

• Shibuya Isao

  National Chemical Laboratory for Industry

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• The reaction of 2,4,6-triphenyl-1,3-thiazinylium perchlorate with active methylenes.

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