Chemistry of nitrosoureas. Decomposition of deuterated 1,3-bis(2-chloroethyl)-1-nitrosourea

Abstract

BCNU-.alpha.-d4 [1,3-bis(2-chloro-1,1-dideuterioethyl)-1-nitrosourea] and BCNU-.beta.-d4 [1,3-bis(2-chloro-2,2-dideuterioethyl)-1-nitrosourea] were synthesized and decomposed in buffered (ph 7.4) water. The products were analyzed by gas chromatography-mass spectra. The deuterium distribution in the products was inconsistent with vinylcarbonium ion or diazochloroethane intermediacy but was consistent with a 2-chloroethylcarbonium ion intermediate with some rearrangement to the 1-chloroethylcarbonium ion and the cyclic chloronium ion.