Premium
An efficient method for synthesizing [d 6 ]‐butadiene monoepoxide
Author(s) -
Maples Kirk R.,
Lane Jennifer L.,
Dahl Alan R.
Publication year - 1992
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580310607
Subject(s) - chemistry , epoxide , 1,3 butadiene , in vivo , yield (engineering) , isotope dilution , carcinogen , chromatography , organic chemistry , mass spectrometry , materials science , microbiology and biotechnology , metallurgy , biology , catalysis
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.