A. Tsolomitis, C. Sandris
Nov 1, 1985
Citations
0
Influential Citations
7
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
2-Benzyl-5-mesitoyl-3(2H)-isothiazolone (8) has been prepared from 3-mesitoylpropionic acid (5). Reaction of the isothiazolone 8 with sodium ethoxide in ethanol has been found to yield an isomeric rearranged compound, which was characterized as 2-phenyl-6-mesitoyl-3,4-dihydro-1,3-thiazin-4(2H)-one (9). This unexpected rearrangement is attributed to the abstraction of a benzylic hydrogen atom from the N-benzyl group, followed by ring enlargement through cleavage of the isothiazolone SN bond.