Synthesis of perdeuterated analogues of the epoxide metabolites of butadiene: 1,2-epoxybut-3-ene-d6 and 1,2,3,4-diepoxybutane-d6

Deuterated analogues of the carcinogenic metabolites of 1,3-butadiene (BD) 1,2-epoxybut-3-ene (EB) and 1,2,3,4-diepoxybutane (DEB), which are not commercially available, are conveniently synthesized in good yields by oxidation of BD-d6 with appropriate quantities of dimethyldioxirane (DMDO). Both epoxides were characterized by proton and deuterium NMR and mass spectrometry; yields were quantified by gas chromatography/mass spectrometry using samples of known concentrations of commercially available non-deuterated epoxides as standards. The synthesized DEB-d6 was a mixture of the enantiomeric RR and SS enantiomers and the meso RS diastereomers.