Issue 76, 2013
From the journal:

Chemical Communications

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

Vallyanga Chalil Rojisha,a   Karikkeeriyil Nijesh,a   Susmita De*a  and  Pattiyil Parameswaran*a  

* Corresponding authors

a Department of Chemistry, National Institute of Technology Calicut, Kozhikode, Kerala, India
E-mail: param@nitc.ac.in, susmitade1980@gmail.com
Fax: +91-495-2287250
Tel: +91-495-2285304

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.

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

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Article information

DOI
https://doi.org/10.1039/C3CC44509G
Article type
Communication
Submitted
16 Jun 2013
Accepted
23 Jul 2013
First published
23 Jul 2013

Chem. Commun., 2013,49, 8465-8467

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

V. C. Rojisha, K. Nijesh, S. De and P. Parameswaran, Chem. Commun., 2013, 49, 8465 DOI: 10.1039/C3CC44509G

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