Pioneering the Power of Twin Bonds in a Revolutionary Double Bond Formation. Unveiling the True Identity of <i>o</i>‐Carboryne as <i>o</i>‐Carborene
Jordi Poater, Clara Viñas, Sílvia Escayola, Miquel Solà, Francesç Teixidor
Abstract
Abstract 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‐C 2 B 10 H 12 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.