期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 9, 期 -, 页码 1419-1425出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.159
关键词
DFT calculations; dipolar addition; fluxional behavior; sulfones; VT NMR
资金
- Canadian Institutes of Health Research
- University of Victoria Faculty of Science
- Canada Research Chairs
- Michael Smith Foundation for Health Research programs
- Office of the Vice President of Research at the University of Notre Dame
Dipolar addition of cyclic azomethine imines with cyclic vinyl sulfones gave rise to functionalized tricycles that exhibited fluxional behavior in solution at room temperature. The scope of the synthetic methodology was explored, and the origin of the fluxional behavior was probed by NMR methods together with DFT calculations. This behavior was ultimately attributed to stereochemical inversion at one of two nitrogen centers embedded in the tricyclic framework. Two tetracycles were also synthesized, and the degree of signal-broadening in the NMR spectra was found to depend on the presence of substitution next to the inverting nitrogen center.
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