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Singlet 2-adamantylidene – an ambiphilic foiled carbene stabilized by hyperconjugation

2013; Royal Society of Chemistry; Volume: 49; Issue: 76 Linguagem: Inglês

10.1039/c3cc44509g

1364-548X

Vallyanga Chalil Rojisha, Karikkeeriyil Nijesh, Susmita De, Pattiyil Parameswaran,

Organoboron and organosilicon chemistry

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.