Total Synthesis and Characterization of 7-Hypoquinuclidonium Tetrafluoroborate and 7-Hypoquinuclidone BF3 Complex
| Autor: | Brian M. Stoltz, Michael K. Takase, Marc Liniger, David G. VanderVelde, Mona Shahgholi |
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| Rok vydání: | 2016 |
| Předmět: |
Models
Molecular Quinuclidines Tetrafluoroborate chemistry.chemical_element Crystallography X-Ray 010402 general chemistry 01 natural sciences Biochemistry Article Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Amide Polymer chemistry Organic chemistry Boranes Molecular Structure Bicyclic molecule 010405 organic chemistry 7-hypoquinuclidone Total synthesis General Chemistry Nitrogen 0104 chemical sciences Characterization (materials science) chemistry Anhydrous |
| Zdroj: | Journal of the American Chemical Society. 138:969-974 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.5b11750 |
| Popis: | Derivatives of the fully twisted bicyclic amide 7-hypoquinuclidone are synthesized using a Schmidt–Aubé 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–BF_3 complex of 7-hypoquinuclidone under anhydrous conditions and to react instantaneously with water making it one of the most reactive amides known to date. |
| Databáze: | OpenAIRE |
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