10344. Diphenylphosphoryl Azide
Nomenclature
CAS number: 26386-88-9
Phosphorazidic acid diphenyl ester; diphenyl phosphorazidate; DPPA. C12H10N3O3P; mol wt 275.20.
C 52.37%, H 3.66%, N 15.27%, O 17.44%, P 11.26%.
Description and references
Non-explosive azide transfer reagent; utilized in peptide synthesis, the modified Curtius rearrangement, and other synthetic transformations. Prepn and synthetic utility: T. Shioiri et al., J. Am. Chem. Soc. 94, 6203 (1972) DOI PubMed. Alternate prepn: E. Shi, C. Pei, Synthesis 2004, 2995 DOI. Large scale prepn: O. Wolff, S. R. Waldvogel, ibid. 1303 DOI. Additional synthetic applications: K. Ninomiya et al., Tetrahedron 30, 2151 (1974) DOI; S. Yamada et al., J. Org. Chem. 39, 3302 (1974) DOI; A. S. Thompson et al., ibid. 58, 5886 (1993) DOI. Reviews: A. V. Thomas in Encyclopedia of Reagents for Organic Synthesis vol. 4, L. A. Paquette, Ed. (Wiley, New York, 1995) pp 2242-2245; H. Liang, Synlett 2008, 2554-2555 DOI.
