Abstract
The EDA-NOCV analysis shows that the singlet 2-adamantylidene is a foiled-type carbene stabilized by the hyperconjugative interaction of one pair of the vicinal C-C σ-MOs with the empty p-orbital on the carbene carbon atom. The high proton affinity and hydride affinity indicate the ambiphilic nature of 2-adamantylidene.
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