Chemoselective C–C s-Bond Activation of the Arene Ring of Biphenylene

DOI: 10.14469/hpc/7325 Metadata

Created: 2020-08-05 12:33

Last modified: 2020-08-27 07:54

Author: Richard Yuze Kong

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)


The chemoselective cleavage of an arene ring in biphenylene is reported using an aluminium (I) complex. The reaction proceeds with complete integrity of the central 4-membered ring. Density functional theory calculations show that a (4+1) cycloaddition of the aluminium (I) complex to the arene ring determines the chemoselectivity of the reaction. Activation strain analysis is used to understand the origins of chemoselectivity of the reaction. Both the symmetry and diffuseness of the frontier molecular orbitals of the aluminium (I) fragment are implicated in its divergence from canonical reactivity towards biphenylene.


10.14469/hpc/7345 NMR Data
10.14469/hpc/7346 Computational Coordinates