Phosphorazidic acid diethyl ester

Phosphonic acid, (phthalimidomethyl)-, diethyl ester, 65, 119 Phosphorazidic acid, diphenyl ester (26386-88-9), 68,1 Phosphoric triamide, hexamethyl- (680-31-9), 66, 51, 94 Phosphorodichloridic acid, 2-chloroethyl ester, 65, 68 Phosphorous acid, triethyl ester, 65, 108.119 Phosphorus oxychloride, 66,173, 176 67,1 68, 41,162 Phosphorus tribromide (7789-60-8), 67, 210 Phthalimide, N-(bromoethyl)-, 65, 119 Phthalimide, N-(hydroxymethyl)-, 65,119 Pig liver esterase, 69, 20... 

Diethyl phosphorocyanidate continues to be exploited for the purposes of conventional organic synthesis. Reported applications of the compound include a new conversion of carboxylic acids into esters or amides and also a ring-expansion reaction of 1,3-thiazoles in the penicillin series. Diphenyl phosphorazidate has been employed in a modified Curtius reaction/ in peptide synthesis, and for... 

A further example of the value of thioesters as acyl transfer agents is the production of esters from these reagents by reaction with an alcohol and N-bromosuccinimide. ° Both thio- and seleno-esters are readily available from free acids via the intermediacy of the acid imidazolide or 1,2,4-triazolide, which react smoothly with thiols or selenols to give the desired esters in high overall yields. Thioesters can also be prepared directly from free acids and thiols by condensation in the presence of either diphenyl phosphorazidate or diethyl phos-phorocyanidate. S-Ethylthioesters can be obtained, generally in high yields, by... 

Yokoyama, Y., Shioiri, T., and Yamada, S., Phosphorus in organic synthesis. Part 16. Diphenyl phosphorazidate (DPPA) and diethyl phosphorocyanidate (DEPC). Two new reagents for the preparation of thiol esters from carboxylic acids and thiols, Chem. Pharm. Bull., 25, 2423, 1977. 

Novel synthetic routes to thiol-esters use carboxylic acids and thiols with diethyl phosphorocyanidate or diphenyl phosphorazidate, and EtjN in DMF, ... 

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