Synthesis and Reactions of Methylene-bridged Polycyclic Aromatic Hydrocarbons

Abstract

Although methylene-bridged polycyclic aromatic hydrocarbons (PAH) are important environmental pollutants, little is known concerning their chemical and biological properties. In order to make PAHs of this class available, we have devised syntheses of a series of bridged polyarenes. We also investigated their patterns of electrophilic substitution in relation to MO theoretical predictions, and explored synthetic routes to oxidized derivatives bearing an OH or a C=O function on the bridge site. There is evidence that the bridge alcohol derivatives are metabolized to sulfate esters that react with DNA leading to tumorigenesis.

Key Words:

• 4H-Benzo[c]cyclopenta[mno]chrysene
• 13H-dibenz[bc, l]aceanthrylene
• 6H-cyclopenta[ghi]picene
• 13H-cyclopenta[rst]pentaphene
• 12H-benzo[b cyclopenta[def]chrysene
• methylene-bridged PAH.