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The Action of Carbon Disulfide and Sulfur on Enamines, Ketimines, and CH Acids

Authors

  • Prof. Dr. Roland Mayer,

    1. Institut für Organische Chemie der Technischen Universität, Mommsen-Str. 6, X 8027 Dresden (Germany)
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  • Doz. Dr. K. Gewald

    Corresponding author
    1. Institut für Organische Chemie der Technischen Universität, Mommsen-Str. 6, X 8027 Dresden (Germany)
    • Institut für Organische Chemie der Technischen Universität, Mommsen-Str. 6, X 8027 Dresden (Germany)
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  • Part 64 of Organic Compounds of Sulfur; Part 63: J. Morgenstern and R. Mayer, J. prakt. Chem. [4], 34, 116 (1966).

Abstract

The reaction of sulfur, carbon disulfide, and enamines at room temperature leads mainly or exclusively to 3H-1,2-dithiole-3-thiones; these are occasionally accompanied by 2H-1,3-dithiole-2-thiones, which can also be prepared by a modified procedure. Many enamines react with sulfur at room temperature to form thioamides. At about 50°C, enamines of acetophenone give 2-benzylidene-4-phenyl-2H-1,3-dithiol. The action of isothiocyanates and sulfur on enamines leads to the formation of thiazolidine-2-thiones. 2H-Thiopyran-2-thiones can be prepaAred from enamines or dienamines with carbon disulfide at room temperature. The reaction of ketimines (Schiff bases) with carbon disulfide and sulfur yields 3H-1,2-dithiole-3-thiones or isothiazoline-5-thiones. The reaction of alkynes with sulfur and carbon disulfide leads to 2H-1,3-dithiole-2-thiones. Nitriles containing active methylene groups react with carbon disulfide and sulfur to form 5-amino-3H-1,2-dithiole-3-thiones. When isothiocyanates are used instead of CS2, the reaction leads to δ4-4-amino-thiazoline-2-thiones.

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