Abstract
The beta-shielded acrylamide N,N-diisopropyl-alpha-(1,1,3,3-tetramethylindan-2-ylidene) acet-amide was prepared through ketone addition of an alpha-lithiated acetamide, followed by H2O elimination. Its alpha-deprotonation by n-butyllithium occurred readily in THF without any tendency towards addition reactions at C=O or C-beta. The resultant single crystals of a dimeric lithio derivative had triple Li-O coordination and a weakly bonding, ion-pair type Li-C(alpha) relationship. In tert-butyl methyl ether as the solvent, up to seven pairs of diastereotopic nuclei (both H-1 and C-13) established a C-S-symmetric lithium 1-aminoallen-1-olate structure that is ascribed to either a thermal ground state or a very rapid (on the NMR time scales) oscillation between two chiral ground states that may resemble the solid-state structure. (c) 2019 Elsevier B.V. All rights reserved.
Dokumententyp: | Zeitschriftenartikel |
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Fakultät: | Chemie und Pharmazie > Department Chemie |
Themengebiete: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
ISSN: | 0022-328X |
Sprache: | Englisch |
Dokumenten ID: | 83328 |
Datum der Veröffentlichung auf Open Access LMU: | 15. Dez. 2021, 15:07 |
Letzte Änderungen: | 15. Dez. 2021, 15:07 |