S. N. Lewis, G. A. Miller, M. Hausman
Aug 1, 1971
Citations
1
Influential Citations
66
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The syntheses of 3-hydroxyisothiazole, 4-methyl-3-hydroxyisothiazole, and a eomprehensive series of the respective 2-substituted-4-isothiazoIin-3-ones have been achieved by the one-step chlorination-cyclization of the corresponding 3,3 -dithiodipropionamides. In several instances, 5-chloro-4-isothiazolin-3-ones were isolated as side products; however, no 4-chloro-4-isothiazo-lin-3-ones were evident in the reaction mixtures. These observations, coupled with the exclusive 4- or 4,5-halogenation of several preformed 4-isothiazoIin-3-ones, support a proposed reaction pathway involving introduction of chlorine α to the sulfur atom in intermediate reaction products.