AN EFFICIENT METHOD FOR SYNTHESIZING [D(6)]-BUTADIENE MONOEPOXIDE

Epoxides are known mutagenic and carcinogenic metabolites of alkenes. During current toxicological investigations in our laboratory, we have monitored in vivo epoxide levels using gas chromatography/mass spectroscopy isotope dilution assays. These assays require the use of deuterated analogues for the expected epoxide metabolites. To determine whether butadiene monoepoxide is formed in vivo following inhalation of 1,3-butadiene, deuterated butadiene monoepoxide, a compound that is not commercially available, was needed. To meet this need, we developed a method using monoperoxyphthalic acid to synthesize [d6]-butadiene monoepoxide from [d6]-1,3-butadiene with a reaction time of 50 min and a 94% yield.