Synthetic, mechanistic, and structural studies related to 1, 2, 4-dithiazolidine-3, 5-dione

…, TR Thompson, RP Hammer, G Barany

Index: Chen, Lin; Thompson, Tracy R.; Hammer, Robert P.; Barany, George Journal of Organic Chemistry, 1996 , vol. 61, # 19 p. 6639 - 6645

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Citation Number: 26

Abstract

Reaction of O-ethyl thiocarbamate (4) with (chlorocarbonyl) sulfenyl chloride (5) gives 3- ethoxy-1, 2, 4-dithiazolin-5-one (2) and 3, 5-diethoxy-1, 2, 4-thiadiazole (3), with the relative amounts of 2 and 3 formed depending very much on the solvent (eg, diethyl ether favors 2; chloroform favors 3). The effects of added base, order of addition, concentration, and temperature were also studied. Mechanisms for the observed transformations have been ...