Very Important Paper in CEJ! Unveiling the True Identity of o-Carboryne as o-Carborene

The homolytic elimination of two H atoms from two adjacent carbons in benzene results in the aromatic product o-benzyne. In a similar way, the homolytic elimination of two H atoms from the two adjacent carbons in 1,2-C₂B₁₀H₁₂ results in the aromatic product o-carboryne. In this work, we provide experimental and computational evidences that despite the similarity of o-carboryne and o-benzyne, the nature of the C−C bond generated between two adjacent carbons that lose H atoms is different. While in o-benzyne the C−C bond behaves as a triple bond, in o-carboryne the C−C bond is a double bond. Therefore, we must stop naming 1,2-dehydro-o-carboryne as o-carboryne but instead call it o-carborene.

Chemistry A European Journal 2023, 29, e202302448. DOI: 10.1002/chem.202302448. VIP ARTICLE