Improved Synthesis and X-Ray Crystallographic Structure Determination of the Stereoisomeric K-Region Arene Dioxides of Pyrene and Dibenz[a, h]Anthracene [1]

Abstract

In the work reported here we describe an improved procedure for the use of dimethyl-dioxirane, 1, to prepare arene dioxides as well as the isolation and X-ray structure determination of the stereoisomeric dioxides from pyrene, 2, and dibenz[a, h]anthracene, 3. In the case of 2 the dioxides are formed in a 75:25 ratio (cis/trans) and for 3 the dioxide ratio is 45:55 (cis/trans). The X-ray crystallographic structures of both cis dioxides reveal that the oxide groups confer a curvature to the molecular structures.

Key Words:

• Dimethyldioxirane
• PAH carcinogenesis
• pyrene
• dibenz[a, h]anthracene
• arene dioxides