Allyl isothiocyanate, synthesis

The intra- and intermolecular carbon—heteroatom bond forming reactions using alkenyl epoxides and aziridines have been utilized for the synthesis of heterocyclic compounds.261 There are two major processes for the preparation of heterocycles using these substrates, as illustrated in Scheme 192 (a) intramolecular allylation of alkenyl epoxides and aziridines with Y—H and (b) intermolecular cycloaddition of vinyl epoxides and aziridines with the hetero-cumulenes 627, such as isocyanates, carbodiimides, and isothiocyanates.270... 

The reactions of isothiocyanates with a-mercaptoacetic acid continue to be the major method for the synthesis of rhodanines. A facile and uniform procedure for the large-scale preparation of some iV-alkyl-rhodanines has been reported, which involves allowing a primary amine RNH2 (R = Me, Et, allyl, or PhCHa) to react with carbon disulphide and ammonia, followed by treatment of the resulting ammonium alkyldithiocarbamate RNHC(S)S NH4+ with chloro-... 

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