Pioneering the Power of Twin Bonds in a Revolutionary Double Bond Formation. Unveiling the True Identity of o‐Carboryne as o‐Carborene

Abstract

AbstractThe 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.