期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 16, 页码 5560-5568出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b01849
关键词
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资金
- ERC (Advanced Research Grant) [SUPRADAPT 290585]
- ANR DYNAFUN [ANR-15-CE29-0009-01]
- USIAS
- University of Strasbourg
- China Scholarship Council
- ERC
Fast and reversible dynamic covalent C=C/C=N exchange takes place without catalyst in nonpolar solvents between barbiturate-derived Knoevenagel (Kn) compounds and imines. A detailed study of the reaction indicates that it proceeds by an associative organo-metathesis mechanism involving the formation of a four-membered ring azetidine intermediate by addition of the imine C=N group to the C=C bond of the Kn compound. This intermediate could be generated cleanly and stabilized at low temperature by condensation of the o,p-dinitrophenyl Kn derivative with the cyclic imine 1-azacyclohexene. It was characterized by extensive NMR and mass spectrometric studies. The process described represents a genuine dynamic covalent organo-metathesis through a four-membered ring adduct as intermediate. It paves the way for the exploration of a wide set of dynamic systems involving (strongly) polarized C=C bonds and various imines, extending also into covalent dynamic polymers and polymolecular assemblies.
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