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An efficient method for synthesizing [d6]-butadiene monoepoxide

✍ Scribed by Kirk R. Maples; Jennifer L. Lane; Alan R. Dahl


Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
238 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

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 [d~6~]‐butadiene monoepoxide from [d~6~]‐1,3‐butadiene with a reaction time of 50 min and a 94% yield.


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