
TY  - JOUR
A1  - Crow, WD 
A1  - Gosney, I 
T1  - Isothiazole chemistry. III. Kinetics and mechanism of cyclization of <I>cis</I>-3-Thiocyanoacrylamide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1966
VL  - 19
IS  - 9
SP  - 1693
EP  - 1699
KW  - 
UR  - https://doi.org/10.1071/CH9661693 
N2  - The cyclization of cis-3-thiocyanoacrylamide to isothiazol-3-one has been studied over the pH range 0-5.5 and it is shown that two cyclization mechanisms exist. Within the pH range 5.5-3.5, the only important mechanism is one involving a rapid, unimolecular cyclization of the thiocyanoacrylamide anion, while at pH less than 3.00, the process is essentially a slow cyclization of the neutral molecule, followed by rapid proton loss. The large rate difference between the two mechanisms is ascribed to a lowering of &#916;F* in the anion cyclization mechanism by a more favourable T&#916;S* term, and possible reasons for this are discussed. 
ER  -

