期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 23, 期 34, 页码 8161-8165出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201701781
关键词
1,3-diyne; cyclization; hydride transfer; keteniminium; pyranopyridine; ynamide
资金
- NSF [CHE 1361620]
- NSFC [21372178, 21572163]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361620] Funding Source: National Science Foundation
A facile thermal cyclization of ynamide-tethered 1,3,8-triynes to form a 3,5,6,7-tetrahydro-1H-pyrano[3,4c]pyridine skeleton is described. Although the mechanism of this unusual reaction has yet to be defined, the formation of either a strained keteniminium or a biradical intermediate followed by a 1,5-hydride or -hydrogen shift is tentatively proposed as the key elementary steps in the reaction sequence. Appropriate electronic activation at the carbon center donating a hydride or hydrogen is crucial for successful cyclization.
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