Diethyl phosphorobromidate

A synthetic approach to /3-sultams containing a direct bond between a tri- or tetracoordinated phosphorus atom and the nitrogen atom of the 1,2-thiazetidine 1,1-dioxide ring has been realized by direct phosphitylation or phosphorylation at nitrogen. Unfortunately, attempts to synthesize N-phosphorylated /3-sultams by reaction with diethyl phosphorochloridate and diethyl phosphorobromidate, generated in situ from diethyl phosphate and carbon tetrachloride or carbon tetrabromide, failed. However, when the /3-sultam is treated with freshly distilled diethyl phosphorochloridite or tetramethylphosphorodiamidous chloride in the presence of triethylamine, the expected AHliethy I phosphite and iV-phosphorodiamidous /3-sultams 150 are obtained (Equation 10). /3-Sultams unsubstituted... 

Gorecka, A., Leplawy, M., Zabrocki, J. and Zwierzak, A. (1978) Diethyl phosphorobromidate - an effective new peptide-forming agent. Synthesis, 474 -76. 

AMIDES Aluminum chloride-Ethanol. Diethyl phosphorobromidate. Di-methylaluminum amides. 2-Fluoro-... 

Related Reagents. Diethyl Phosphorobromidate Diethyl Phosphorocyanidate. 

These compounds can be prepared by the action of bromine c i a trialkyl phosphite, but a more satisfactory method recently worked out by Goldwhite and Saunders consists in treating the dialkyl hydrogen phosphite with W-bromosuccinimide. In this way dimethyl, diethyl -propyl and isopropyl phosphorobromidates have been obtained as pure liquids by distillation at very low temperature. When kept at ordinary temperatures, they gradually decompose with the evolution of the corresponding alkyl bromide. 

Diethyl dithio-phosphate Dialkyl phosphoro-chloridate, (C,H,0)2P0CI Pyrocatechyl phos-phorochloridate - phosphorobromidate Phenylphosphonic dichloride Phenyl phosphoryl dichloride (C, )2NPOCl2 Pyrocatechyl phos-phorotrichloridate, -tribromidate Phosphate buffer (HPO,),... 

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