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Dithiocarboxylic Acids, Dithiocarboxylic Esters, or Thiocarboxylic Amides by Reaction of Methylene-active Chloromethyl Compounds with Sulfur
Thiel, W.,Mayer, R.
, p. 243 - 262 (2007/10/02)
With a mixture of sulfur and amine in DMF at room temperature halomethyl compounds (1,5-10) can be oxidized to give thiocarboxylic acids (2,11-16) and their derivatives (3,4,17-35).We studied this reaction in detail especially with chloroacetic derivatives (11-15) or chloromethyl heterocycles (16) formally derived from chloroacetic acid.The resulting thiooxalic acid derivatives (11-27) represent activated acids and very useful C2-synthons, especially for the synthesis of heterocycles.Oxidation in the presence of triethylamine leads to dithiocarboxylates (11-16) which can be alkylated to dithioesters (17-27) in high yields.As a rule, with different primary and secondary amines instead of tertiary amines these dithiocarboxylates or dithiocarboxylic esters can be transformed already at low temperatures to thioamides (28-35).
