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CO Fixation to Stable Acyclic and Cyclic Alkyl Amino Carbenes: Stable Amino Ketenes with a Small HOMO–LUMO Gap
Author(s) -
Lavallo Vincent,
Canac Yves,
Donnadieu Bruno,
Schoeller Wolfgang W.,
Bertrand Guy
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200600987
Subject(s) - lone pair , alkyl , chemistry , diradical , amino acid , stereochemistry , medicinal chemistry , organic chemistry , molecule , physics , quantum mechanics , singlet state , excited state , biochemistry
A quick fix : In contrast to cyclic diamino carbenes, stable alkyl amino carbenes react with CO to give stable ketenes (see scheme, top). Contrary to the acyclic versions, cyclic amino ketenes cannot escape from the destabilizing n–π donation of the nitrogen lone pair, which induces a diradical character and unusual optical (see scheme, bottom and photographs of crystals) and NMR spectroscopic properties.