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■ Reactions of Monohalomethyl Aryl Ketoximes with Tetrasulfur Tetranitride: Much Improved Synthesis of 3-Aryl-1,2,5-thiadiazoles

Kyongtae Kim* and Jaeeock Cho

*Department of Chemistry, Seoul National University, San 56-1, Shillim-Dong, Kwanak-Gu, Seoul 151-742, Korea

Abstract

Reactions of chloromethyl aryl ketoximes (1, X = Cl) with tetrasulfur tetranitride in p-dioxane at reflux for 4 h afforded 3-aryl-1,2,5-thiadiazoles (2) in 37-92% yields, whereas those of bromo analogs under the same conditions gave 2 and 3-aryl-4-bromo-1,2,5-thiadiazoles (3) in 48-81% and 17-31% yields, respectively. However, the compounds (3) were not formed in the presence of pyridine. α-Nitrosostyrene and its ring-substituted derivatives (4) are proposed as intermediates for the formations of 2.