Thiocarbamyl azides

The procedure is essentially similar to that described for the preparation of 5-amino-l,2,3,4-thiatriazole. Freund and Hempel6,7 have reported observing that the initial diazotization products of 4-aryl-substituted thiosemicarba-zides lead to the formation of tetrazoles, while the corresponding 4-alkyl-substituted thiosemicarbazides were considered by Freund and Schwarz8 to be thiatriazoles. However, Oliveri-Mandala,9 on the basis of his study of the reaction of alkyl and aryl isothiocyanates with hydrazoic acid, concluded that the initial diazotization product of either 4-aryl or 4-alkyl thiosemicarbazides were open-chain thiocarbamyl azides, RNHC( S)N3. Lieber, Pillai, and Hites10 have recently clarified this situation and have shown... 

Thiocarbamyl Azides, Imido Azides, and Hydroximido Azides. Thio-semicarbazides react with nitrous acid and isothiocyanates react with hydrazoic acid to yield azides of marked stability. For this... 

Thiocarbamyl Addes, Imido Azides, and Hydroximido Addes.362... 

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