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.
| Original language | English |
|---|---|
| Pages (from-to) | 1479-1482 |
| Number of pages | 4 |
| Journal | Journal of Heterocyclic Chemistry |
| Volume | 22 |
| Issue number | 6 |
| DOIs | |
| State | Published - 1985 |