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 GC-MS. The deuterium distribution in the products is inconsistent with vinylcarbonium ion or diazochloroethane intermediacy but is consistent with a 2-chloroethylcarbonium ion intermediate with some rearrangement to the 1-chloroethylcarbonium ion and the cyclic chloronium ion.