The Synthesis of Thiols by Use of N, N-Dimethylthioformamide

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  • N,N-ジメチルチオホルムアミドを用いるチオールの合成
  • Ｎ，Ｎ‐ジメチルチオホルムアミドを用いるチオールの合成

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Description

The reaction of benzyl chloride with N, N-dimethylthioformamide (DMTF) led to a smooth formation of the S-benzylated adduct which then was decomposed with methanol to give atoluenethiol ( I ) quantitatively. On hydrolysis of the adduct, ( I ) as a main product, Sbenzyl thioformate(iI) and tris(benzylthio)methane(I1) were produced (see Table 2). The decomposition of the adduct ( 1 ) with water appeared to form a gem-amino alcohol intermediate ( 2 ) at first, and the corresponding thiol and the other products were considered to be obtained from the cleavage of the C-S and C-N bonds of ( 2 ) (see Fig.2). In the case of methanolysis, the thiol appeared to be formed preferentially from the cleavage of the C-S bond in the gem-amino alcohol type intermediate. Halides such as hexyl bromide, octyl bromide and methyl chloroacetate easily formed adducts with DMTF. The decomposition of these adducts with methanol gave the corresponding thiols in good yields (see Table 3). The reaction of benzoyl chloride with DMTF geve a small amount of an adduct which, on the hydrolysis, formed thiobenzoic acid in about 30% yield (see Table 1). The decomposition of alkyl halide-DMTF adduct with methanol is concluded to be a good method for synthesizing thiols.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1979 (1), 101-105, 1979-01-10

    The Chemical Society of Japan

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