ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Dithiocarboxylic Acids, Dithiocarboxylic Esters, or Thiocarboxylic Amides by Reaction of Methylene-active Chloromethyl Compounds with SulfurWith 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 triethyl amine 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).
Additional Material:
14 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19893310211
