Abstract
Halide derivatives may be converted directly into their isothiocyanate homologues by the action of thicyanate ions fixed to the macromolecular network of an ion exchange resin. The reaction leads first to the thiocyanate derivative (kinetic product), which is isomerized to the isothiocyanate derivative (thermodynamic product). The isomerisation process depends on both the structure of the halogenated substrate and the nature of the reaction environment. This isomerisation is catalysed by polymer-supported reagents but is inhibited by a protic solvent such as butanol. These results suggest that the ionization and preliminary dissociation of the thiocyanate isomer are followed by an attack on the carbonium ion by the nitrogen atom of the thiocyanate ion.
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