Thionoformates, chloro

Aryloxy- and alkyloxy-l,2,3,4-thiatriazoles have been prepared from azide ion and aryl chlorothionofbrmates " or alkyl chloro-thionoformates , respectively. Alkyloxythiatriazoles are also made from alkyl thionocarbazates and nitrous acid ° °. The subject has been reviewed by Martin . The 5-aryloxy- or 5-alkyloxy-l,2,3,4-thiatriazoles decompose thermolytically in a manner analogous to the decomposition of the other triazoles mentioned above they give nitrogen, sulphur and cyanates. This is the most used route to alkyl and aryl cyanates, R—OGN. The mechanism of this decomposition could be concerted, or it could involve a thioacyl azide ... 

NITRILES 0-Chlorophenyl chloro-thionoformate. Chlorosulfonyl isocyanate. Diphenyl phosphoro-chloridate. 

Acidic reagents seem to offer milder conditions. Dehydration reactions forming cyanides can be performed with phosgene [1049-1052], diphosgene [1053-1055], triphosgene [1056], phenyl chloroformate [1057], oxalyl chloride [1058, 1059], tri-chloroacetyl chloride [1060-1062], acetic anhydride [1063-1074], TFAA [1075-1082], phosphorus oxides [1083-1088], phosphorus oxychloride [1089-1098], phosphorus pentachloride [1099], triphenylphosphine/haloalkanes [1100-1103], thionyl chloride [1104-1118], p-tosyl chloride [1119-1124], triflic anhydride [1125-1127], chlorosulfonyl isocyanate [1128], the Burgess reagent [1129], phenyl chloro-thionoformate [1130], cyanuric chloride [1131-1134], carbodiimides [1135, 1136], CDC [1137], PyBOP [1138], AlCU/Nal [1139], and acetonitrile/aldehyde [1140], and by pyrolysis [1141]. 

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