title: Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formed via alkene metathesis from either a triene or a tetraene precursor.
abstract: 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, a (1)H-(1)H 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 the trans-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 the trans-2,3,6,7-dehydrodecalin-β-cyanohydrin.
authors.affiliation: Chemistry, Imperial College London, London SW7 2AZ, England.
authors.forename: Keith G
authors.initials: KG
authors.lastname: Andrews
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Frampton
authors.forename: Alan C
authors.initials: AC
authors.lastname: Spivey
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*
chemical_list: D000475:Alkenes; D003517:Cyclopentanes; D009570:Nitriles; C586697:bis-cyclopentenyl-beta-cyanohydrin(1-(1-hydroxycyclopent-3-en-1-yl)cyclopent-3-ene-1-carbonitrile); C430593:cyanohydrin
keywords: NMR prediction; alkene metathesis; crystal structure; density functional theory (DFT); euonyminol; ring-closing metathesis (RCM); ring-opening metathesis (ROM)