Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 3, Pages 969-974Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b11750
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Funding
- NIH-NIGMS [R01GM080269]
- Amgen
- Gordon and Betty Moore Foundation
- Caltech Center for Catalysis and Chemical Synthesis
- Caltech
- Swiss National Science Foundation (SNSF) [P2EZP2_148751]
- Swiss National Science Foundation (SNF) [P2EZP2_148751] Funding Source: Swiss National Science Foundation (SNF)
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Derivatives of the fully twisted bicyclic amide 7-hypoquinuclidone are synthesized using a Schmidt-Aube reaction. Their structures were unambiguously confirmed by X-ray diffraction analysis and extensive spectroscopic characterization. Furthermore, the stability and chemical reactivity of these anti-Bredt amides are investigated. 7-Hypoquinuclidonium tetrafluoroborate is shown to decompose to a unique nitrogen bound amide-BF3 complex of 7-hypoquinuclidone under anhydrous conditions and to react instantaneously with water making it one of the most reactive amides known to date.
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