Pioneering the Power of Twin Bonds in a Revolutionary Double Bond Formation. 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.

Automated summary

This study provides experimental and computational evidence that the C-C bond formed between two adjacent carbons that lose H atoms in o-carboryne is different from that in o-benzyne. While the C-C bond in o-benzyne behaves as a triple bond, the C-C bond in o-carboryne is a double bond. Therefore, 1,2-dehydro-o-carboryne should be called o-carborene instead of o-carboryne.