Tetrahedron Letters

Peracid-mediated N-oxidation and rearrangement of dimethylphosphoramides: plausible model for oxidative bioactivation of the carcinogen …

I Holden, Y Segall, EC Kimmel, JE Casida

Index: Holden; Segall; Kimmel; Casida Tetrahedron Letters, 1982 , vol. 23, # 49 p. 5107 - 5110

Full Text: HTML

Citation Number: 17

Abstract

Abstract Dimethylphosphoramides react with m-chloroperoxybenzoic acid (MCPBA) in anhydrous acetone to yield the previously unknown P-dimdethylamino-oxyphosphonous derivatives via N-oxidation and rearrangement. Further MCPBA oxidation yields formaldehyde and nitrosomethane, isolated as its trans-dimer. These reactions provide a possible biomimetic model for the metabolic activation of hexamethylphosphoramide as a ...