Synthesis of Nitriles and Symmetrical Organic Sulphides from Biprotic Carbothioamides and an ?-Halogenated Ketone, Ester or Nitrile
- 1 January 1979
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 9 (7) , 569-573
- https://doi.org/10.1080/00397917908066702
Abstract
Thioacetamide has been used as an elegant sulphur transfer reagent for C-S-C coupling of reactive halides.1–4 Sulphur extrusion of biprotic carbothioamides to form corresponding nitriles has been reported with the help of (i) dichlorocarbene;5 (ii) triphenylphosphine, carbon tetrachloride, triethylamine;6 (iii) diethyl azocarboxylate, triphenylphosphine;7 and (iv) soft metal ions.8 Here, we report that under non-hydrolytic conditions viz. DMF/OEt, EtOH/OEt and DMF/Et3N, biprotic carbothioamides (1, R=CH3, C6H5, CH2C6H5) react with bromoacetophenone (2, Z=COC6H5), ethyl bromoacetate (2, Z=COOEt).Keywords
This publication has 7 references indexed in Scilit:
- A new Method for the Synthesis of Many‐membered Sulfides by Means of ThioacetamideEuropean Journal of Inorganic Chemistry, 1978
- Sulphur extrusion with N,N-dimethylformamide and sodium ethoxide-a convenient synthesis of 4-(1-acyl and acyloxyalkylidene)-3,4-dihydroquinazolinesTetrahedron Letters, 1977
- Metal-ion-promoted reactions of organo-sulphur compoundsChemical Society Reviews, 1977
- New method for converting thioamides into nitriles: use of diethyl azodicarboxylate and triphenylphosphineJournal of the Chemical Society, Chemical Communications, 1977
- Reaction of Hydrazonyl Halides with Primary Thioamides; Formation of Thiohydrazides and Hydrazonyl Sulfides.Acta Chemica Scandinavica, 1976
- A new synthesis of nitrilesTetrahedron Letters, 1973
- Über die gemeinsame Einwirkung von Phosphinen und Tetrachlorkohlenstoff auf Ammoniak (Derivate), II. Eine einfache Nitril‐SyntheseEuropean Journal of Inorganic Chemistry, 1971