| Abstract: | Attempts to thermally rearrange 2-benzothiazolylthioacetonitrile ( 1) to the titled compound 8 failed. The reaction of 3-chloromethyl-2-benzothiazolinethione with potassium cyanide in dimethylformamide (DMF) or dimethylsulfoxide (DMSO) at 25-30° afforded 8 in 98% yield. Whereas replacing the DMF or DMSO solvent with acetone furnished the unexpected sulfide 9 in 92% yield. Substituting 3-chloromethyl-2-benzoxazoline-thione as the electrophile in the same reaction gave the sulfide 10 in 95% yield. Possible mechanisms and supporting nmr data are discussed. |
