63365-55-9

Upstream product

• 100-14-1 4-nitrobenzyl chloride 
• 95417-01-9 Toluene-4-thiosulfonic acid S-[(4-nitro-benzylsulfanyl)-(4-nitro-phenyl)-methyl] ester 
• 1835-71-8 bis(4-nitrobenzyl) sulfide 
• 62740-56-1 (α-Chlor-p-nitrobenzyl)-p-nitrobenzylsulfid 

Relevant academic research and scientific papers

Dithiocarboxylic Acids, Dithiocarboxylic Esters, or Thiocarboxylic Amides by Reaction of Methylene-active Chloromethyl Compounds with Sulfur

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).

Transformation of Thiosulphonates into α-Sulphonyldisulphides, a New Class of Thioaldehyde Precursors

Toluene-p-thiosulphonates, RCH2SSO2Tol (1) where R is an electron-withdrawing group, are transformed readily into α-sulphonyldisulphides (2) which, with triethylamine, undergo fragmentation-elimination to give 2 moles of thioaldehydes, RCHS.