SYNTHESIS OF ALKYL TRITHIOPERESTERS (ALKYL THIOCARBONYL DISULFIDES)

The first synthesis of alkyl trithioperesters (RC(S)SSR', alkyl thiocarbonyl disulfides) is described, tert-Butyl trithiophenylperacetate (4) was synthesized starting with benzyl chloride. The Grignard of benzyl chloride is treated with carbon disulfide and hydrolyzed to give dithiophenylacetic acid (1). The dithio acid 1 was stabilized by formation of the metal salt 2, which was reacted with tert-butylsulfenyl iodide (3) to form the trithioperester 4. Other trithioperesters, tert-butyl trithiophenylperformate (5) and tert-butyl trithioanisylperformate (6), were synthesized by the same general reaction differing only in how the dithio acid was obtained. Preliminary observations concerning the thermal decomposition of tert-butyl trithiophenylperacetate (4) are discussed. © 1979, American Chemical Society. All rights reserved.