Theory of Substituent Effects on the Regioselectivity of Di-π-methane Rearrangements of Dibenzobarrelenes

Abstract

The regioselectivities of the di-π-methane rearrangements of unsymmetrically substituted dibenzobarrelenes have been explored with DFT (UM06-2X). Regioselectivity depends on the intramolecular hydrogen bonding and originates from specific stabilization of the triplet biradical intermediates