Facile synthesis of K-region arene oxides

✍ Scribed by P.J. van Bladeren; D.M. Jerina

• Book ID: 104250259
• Publisher: Elsevier Science
• Year: 1983
• Tongue: French
• Weight: 257 KB
• Volume: 24
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)99806-5

✦ Synopsis

Polycyclic aromatic hydrocarbons react at the K-region with N-bromoacetamide in acetic acid to provide trans-bromohydrin acetates which are readily cyclized to arene oxides. The simplicity of the approach makes radioactive and optically active K-region arene oxides easily available.

K-Region arene oxides are of considerable chemical and biochemical interestl. In addition to their solvolytic and photochemical reactions, they are often major metabolites of the polycyclic aromatic hydrocarbons and can be highly mutagenic'. They are very useful substrates for the study of the mechanism of action of epoxide hydrolase 2 3

and the glutathione S-transferases . A number of syntheses of K-region arene oxides have been described. These include i) ring-closure of 2,2'-biphenyldialdehydes with tris-dimethylaminophosphine 4 . .

, 11) conversion of cis-dihydrodiols via 1,3-dioxolanes to trans-chlorohydrin acetates which are then cyclized with base 5 .,.