J. Jones, A. Kresge
May 1, 1993
Citations
0
Influential Citations
10
Citations
Journal
Journal of Organic Chemistry
Abstract
The acid-catalyzed hydrolysis of S-methyl phenyldiazothioacetate, C 6 H 5 C(=N 2 )COSCH 3 , in aqueous solution at 25 o C was found to occur with the hydronium ion isotope effect k H+ +k D+ =3.08 and to give a Bronsted relation, based on carboxylic acid catalysts, whose exponent is α=0.70. This is taken to mean that the reaction occurs by rate-determining proton transfer to the diazo carbon atom. The principal product of the reaction, however, is α-(methylthio)-α-phenylacetic acid, C 6 H 5 CH(SCH 3 )-CO 2 H, which must be formed by 1,2-shift of the methylthio group