Synthesis of nitriles and symmetrical organic sulphides from biprotic carbothioamides and an α-halogenated ketone, ester or nitrile

Harjit Singh, ; Gandhi, C. S. (1979) Synthesis of nitriles and symmetrical organic sulphides from biprotic carbothioamides and an α-halogenated ketone, ester or nitrile Synthetic Communications, 9 (7). pp. 569-573. ISSN 0039-7911

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Related URL: http://dx.doi.org/10.1080/00397917908066702

Abstract

Thioacetamide has been used as an elegant sulphur transfer reagent for C-S-C coupling of reactive halides. Sulphur extrusion of biprotic carbothioamides to form corresponding nitriles has been reported with the help of (i) dichlorocarbene; (ii) triphenylphosphine, carbon tetrachloride, triethylamine; (iii) diethyl azocarboxylate, triphenylphosphine; and (iv) soft metal ions. 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).

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Deposited On:12 Nov 2010 14:01
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