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Natural Science Forum / Chemistry / Organic Synthesis / February 2006isothiazol-3(2H)-one
can u help me find the mechanism for the reaction between Propiolamide and Potassium thiocyanate to form Isothiazolone (isothiazol-3(2H)-one). if u know about an article or website it will be very helpful 1- Conjugated attack of sulfur from potassium thiocyanate on propiolamide. 2- Formation of ani?n on the nitrogen of the amide. 3- Intramolecular attack of nitrogen on sulfur atom, with cyanide anion operating as leaving group. Certainly, the cyanide anion is not a common leaving-group. In this case it operated in this way because of two favorable facts: intramolecular reaction, and attack on sulfer, which is a good electrophile. Hope it helps. Gabriel Tojo Consultant in Synthetic Organic Chemistry |
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