Phosphorus, Sulfur and Silicon and the Related Elements p. 299 - 309 (2003)
Update date:2022-08-11
Topics:
Hoffmann, Frank
Jaeger, Lothar
Griehl, Carola
The reactions of diphenoxyphosphoryl chloride ((PhO)2P(O)Cl) and different chlorophosphonium salts ([R3PCl]X, R = (CH3)2N, pyrrolidine, X = PF6-, BF4-), respectively, with 7-aza-1-hydroxybenzotriazole (HOAt), 1-hydroxybenzotriazole (HOBt), hydroximinomalonitrile (HOxDCO), and ethyl hydroximinocyanoacetate (HOxO) are described. The structures of the new compounds, which are useful coupling reagents for epimerization-free peptide segment condensation, are discussed on the basis of their 1H, 13C, 31P NMR, and IR spectra. The reactions of (PhO)2P(O)Cl lead to mixtures of O- and N-phosphorylated isomers of varying ratios. Contrary, reactions of chlorophosphonium salts yield exclusively one isomer.
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