Thioacyl dithiophosphate

Aryl- and 5-heteroaryl-l,2,3,4-thiatriazoles 9 are quite stable and can also be prepared by the reaction of aromatic (respectively heteroaromatic) carbodithioates <1961ACS1104> or A-thioacyl dithiophosphates 141 <2002J(Pl)1271> with sodium azide (Equation 12). 

The 5-substituted 1,2,3,4-thiatriazoles 758 are prepared by the generation of intermediate azidothiocarbonyl compounds 757 followed by 1,5-electrocyclic reaction (Scheme 326). The intermediate compounds 757 have never been isolated they can be generated by treatment of derivatives of thiohydrazides 756 with either nitrous acid or with arenediazonium salts, and in reactions of thiophosgene (or dithiocarboxylates) 755 (X = Cl, SR) with either sodium- or trimethylsilyl azide (Scheme 326) . For example, thiatriazoles 760 can be prepared in high yields by the reaction of or A-thioacyl dithiophosphates 759 with sodium azide (Scheme 327) <2002J(P1)1271>. 

Treatment of acyl chlorides with a 2-sulfenyl-2-thioxo-l,3,2-dioxaphos-phinane 91 gives the corresponding thioacyl dithiophosphates 92 (Scheme 23)... 

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