Mono- and Diaminocarbenes from Chloroiminium and -amidinium Salts: Synthesis of Metal-Free Bis(dimethylamino)carbene
- 6 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (4) , 1016-1017
- https://doi.org/10.1021/ja0393325
Abstract
Bis(trimethylsilyl)mercury cleanly reacts at low temperature with chloroamidinium and -iminium chlorides, generating persistent metal-free cyclic and acyclic diaminocarbenes, as well as transient aryl-, chloro-, and hydrogenoaminocarbenes; with the latter, the corresponding olefin dimers were isolated, whereas with the former, no dimerization processes were observed.Keywords
This publication has 30 references indexed in Scilit:
- Basicity of a Stable Carbene, 1,3-Di-tert-butylimidazol-2-ylidene, in THF1Journal of the American Chemical Society, 2002
- N-Heterocyclic Carbenes: A New Concept in Organometallic CatalysisAngewandte Chemie International Edition in English, 2002
- Transition-metal systems bearing a nucleophilic carbene ancillary ligand: from thermochemistry to catalysisPublished by Elsevier ,2000
- Stable CarbenesChemical Reviews, 1999
- Diaminocarbenes; Calculation of Barriers to Rotation about Ccarbene−N Bonds, Barriers to Dimerization, Proton Affinities, and 13C NMR ShiftsThe Journal of Physical Chemistry A, 1999
- Complexation of stable carbenes with alkali metalsChemical Communications, 1999
- Bis(N-piperidyl)carbene and its slow dimerisation to tetrakis(N-piperidyl)etheneChemical Communications, 1997
- Crystal Structure of the Dimeric (4‐tert‐Butylthiazolato)(glyme)lithium: Carbene Character of a Formyl Anion EquivalentAngewandte Chemie International Edition in English, 1995
- Stable carbenes as strong basesJournal of the Chemical Society, Chemical Communications, 1995
- Electronic structure of a stable nucleophilic carbeneThe Journal of Physical Chemistry, 1991