Boron-Nitrogen-Containing Benzene Valence Isomers

Benzene is one of the most ubiquitous structural motifs in chemistry. The valence isomers of benzene have also attracted synthetic chemists' attention due to their unique structures, bonding, and reactivity. We have been investigating boron-nitrogen-containing benzene valence isomers via photoisomerization of 1,2-azaborines. In this contribution, we summarize recent developments of these highly strained BN-heterocyclic compounds including their synthesis, characterization, proposed mechanism of formation, and their potential applications. Valence isomers of benzene have long attracted both synthetic and theoretical chemists due to their unique bonding and chemical reactivity. What new chemistry can be unlocked by introducing isosteric boron and nitrogen atoms in these structures? This concept paper highlights the recent development of boron(B)-nitrogen(N)-containing benzene valence isomers, specifically, BN-Dewar benzene and BN-benzvalene. image