Synthesis and rearrangement of Dewar benzenes into biaryls: Experimental evidence for conrotatory ring opening

Abstract

Rearrangement of aryl-substituted Dewar benzenes into the corresponding biaryls may serve as an alternative pathway for synthesis of sterically hindered biaryls. The kinetic data obtained from thermal rearrangements of Dewar benzenes provide experimental evidence for the proposed orbital-symmetry-controlled electrocyclic ring opening.

Keywords

• Dewar benzene
• biaryls
• akynes
• Hammett
• rearrangement
• acetylenic oligophenylene macrocycles
• electrocyclic reactions
• valence isomerization
• zirconacyclopentadienes
• derivatives
• complexes
• stereoselectivities
• hexamethylbenzene
• cyclobutadiene