RESEARCH DEFENCE SOCIETY: Special Appeal

α,β‐unsaturated‐1,2,5‐thiadiazoles

“…In conjunction with our investigation of the chemistry of 1,2,5-thiadiazoles it was noted that few convenient synthetic routes to a!Q-unsaturated-l,2,5-thiadiazoles were available (1). We wish to report a facile synthesis of this class of 1,2,5-thiadiazoles employing the Wittig Reaction (2).…”

“…The synthesis of 3-chloromethyl-l,2,5-thiadiazole (1) was readily effected by the procedure of Gill (1). In this procedure, 1,2,5-thiadiazole-3-carboxylic acid (4,5) is .…”

“…converted to the corresponding acid chloride. This in turn is reduced with sodium borohydride to the corresponding carbinol, which when treated with thionyl chloride affords good yields of 3-chloromethyl-l,2,5-thiadiazole (1). Condensation of halide I with triphenylphosphine took place smoothly in refluxing toluene, giving 3-( 1,2,5-thiadiazolyl-methy1)triphenylphosphonium chloride (11) in 66% yield.…”