Synthesis and Cyclization Reaction of 2-(Hydroxyimino)alkyl N,N-Dialkylthiocarbamates, S-[2-(Hydroxyimino)alkyl] O-Methyl Dithiocarbonate, and Alkyl 2-(Hydroxyimino)alkyl Trithiocarbonates

Masaru Ishida; Kiyoshi Ichikawa; Masahiko Asano; Hirofumi Nakanishi; Shinzi Kato

doi:10.1055/s-1987-27940

Synthesis 1987; 1987(4): 349-353
DOI: 10.1055/s-1987-27940

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Synthesis and Cyclization Reaction of 2-(Hydroxyimino)alkyl N,N-Dialkylthiocarbamates, S-[2-(Hydroxyimino)alkyl] O-Methyl Dithiocarbonate, and Alkyl 2-(Hydroxyimino)alkyl Trithiocarbonates

Masaru Ishida^* , Kiyoshi Ichikawa, Masahiko Asano, Hirofumi Nakanishi, Shinzi Kato

^*Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-11, Japan

Abstract

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2-(Hydroxyimino)alkyl dialkyldithiocarbamates and alkyl 2-(hydroxyimino)alkyl trithiocarbonates react with tosyl isocyanate as dehydrating agent to give bis(4-isothiazolyl) disulfides in moderate yields. However, treatment of S-[2-(hydroxyimino)phenylethyl] O-methyl dithiocarbonate with tosyl isocyanate affords a novel heterocycle 3-phenyl-4H-1,5,2-oxathiazine-6-thione, in 49% yield.

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