Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor
| Autor: | Christopher S. Frampton, Alan C. Spivey, Keith G. Andrews |
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| Rok vydání: | 2013 |
| Předmět: |
chemistry.chemical_classification
Magnetic Resonance Spectroscopy Natural product Molecular Structure Alkene Stereochemistry Cyclopentanes General Medicine Crystal structure Alkenes Crystallography X-Ray Metathesis Polyene Catalysis General Biochemistry Genetics and Molecular Biology chemistry.chemical_compound chemistry Nitriles Density functional theory Cyanohydrin Acyclic diene metathesis |
| Zdroj: | Acta Crystallographica Section C Crystal Structure Communications. 69:1207-1211 |
| ISSN: | 0108-2701 |
| Popis: | The identity of the major product of Ru-catalysed alkene metathesis of two polyene substrates has been determined using density functional theory (DFT) NMR prediction, a1H–1H Total Correlated Spectroscopy (TOCSY) NMR experiment and ultimately by single-crystal X-ray crystallography. The substrates were designed as those that would potentially allow expedient access to thetrans-decalin skeleton of the natural product (−)-euonyminol, but the product was found to be a bis-cyclopentenyl-β-cyanohydrin [1-(1-hydroxycyclopent-3-en-1-yl)cyclopent-3-ene-1-carbonitrile, C11H13NO] rather than thetrans-2,3,6,7-dehydrodecalin-β-cyanohydrin. |
| Databáze: | OpenAIRE |
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