期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 29, 页码 11964-11967出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja305581f
关键词
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资金
- NSFC
- 973 Program [2011CB808700]
A series of 2,6-diazasemibullvalenes (NSBVs) were synthesized and isolated from the reaction of 1,4-dilithio-1,3-dienes with nitriles via oxidant-induced C-N bond formation. For the first time, the activation barrier, and an X-ray crystal structure of a substituted 2,6-diazasemibullvalene were determined. All NSBVs show extremely rapid aza-Cope rearrangement in solution, but the rapid aza-Cope rearrangement is frozen in the solid state, as shown by solid-state NMR measurements and Xray single-crystal structural analysis. Insertion of unsaturated compounds or a low-valent metal center into the NSBV C-N bond gave diverse and interesting ring-expansion products. Theoretical analysis showed that the localized structure is predominant and that the homoaromatic delocalized structure exists as a minor component in the equilibrium.
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