Browsing by Author "Keay, Brian A."
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- ItemOpen AccessTHE 1,4 C-O SILYL MIGRATIONS OF VARIOUS FURAN AND THIOPHENE SYSTEMS(Elsevier, 1989) Keay, Brian A.; Spinazze, Patrick G.
- ItemOpen AccessTHE 1,4-0->C SILYL MIGRATIONS OF VARIOUS 3-[(TRIALKYLSILYL)-OXYMETHYL]-FURANS AND -THIOPHENES(Elsevier, 1987) Keay, Brian A.; Bures, Edward J.
- ItemOpen Access1-Borabarrelene Derivatives via Diels-Alder Additions to Borabenzenes(American Chemical Society, 2006) Wood, T.K.; Piers, W.E.; Keay, Brian A.; Parvez, M.
- ItemOpen Access3,3'-Disubstituted BINAP Ligands: Synthesis, Resolution, and Applications in Asymmetric Hydrogenation(American Chemical Society, 2005) Hopkins, J. Matthew; Dalrymple, Sean A.; Parvez, Masood; Keay, Brian A.
- ItemOpen AccessAcetals of y-oxo-a,B-unsaturated esters in nitrone cycloadditions. Regio- and stereochemical implications(Elsevier, 2001) Keay, Brian A.; Alibes, Ramon; Busque, Felix; de March, Pedro; Figueredo, Marta; Font, Josep; Gambino, Maria Esmeralda
- ItemOpen AccessAnomalous 5-endo-trig reversals: general reactions of 7-oxabicyclo[2.2.1] heptenes and heptanes(National Research Council Canada, 1984-06) Keay, Brian A.; Rajapaksa, D.; Rodrigo, R.
- ItemOpen AccessAvoiding the classical resolution during the synthesis of MeO-BIPHEP and 3,3-disubstituted derivatives(Elsevier, 2005) Keay, Brian A.; Gorobets, Evgueni; Wheatley, Bronwen M. M.; Hopkins, J. Matthew; McDonald, Robert
- ItemOpen AccessBoron-containing aromatic compounds: synthesis, characterization and reactivity(2009) Wood, Thomas Kuchurean; Piers, Warren E.; Keay, Brian A.Boron-containing derivatives of barrelene and benzobarrelene were generated in good to excellent yields by Diels-Alder reactions between Lewis base-stabilized borabenzene and strong dienophiles. The resultant Diels-Alder adducts were more stable when the Lewis base donor atom was nitrogen as opposed to phosphorus. All members of the family were found to be highly Lewis acidic, and the neutral donors which ligated the boron atom could not be removed/exchanged. Most compounds exhibited a high degree of thermal stability and underwent ill-defined decomposition only when heated to temperatures in excess of 200 °C. In selected cases the Diels-Alder reaction was found to be reversible and the free borabenzene, formed transiently through a retro-Diels-Alder reaction, could be trapped if a stronger dienophile was present in solution. When one of the barrelenes was treated with 3,6-di(2-pyridyl)-1,2,4,5-tetrazine, acetylene was removed to give the first 2,3-disubstituted borabenzene pyridine adduct. Additionally, syntheses were developed for boron-doped versions of the larger acenes: anthracene, naphthacene and pentacene. Boron-doped acenes, 9-boraanthracene, 5-boranaphthacene, and 6-borapentacene, were generated upon deprotonation of appropriately constructed precursors in which the boron atom was ligated by an Arduengo carbene (1,3-bis(2,4,6-trimethyl)imidazolidin-2-ylidene ). These molecules were more highly coloured than their corresponding all-carbon counterparts, an observable manifestation of their much smaller HOMO-LUMO gap. This decrease in HOMO-LUMO gap was found to be a result of an increase in the energy of the HOMO, and is attributable to the boron's presence in the acene's n system. Additionally, the smallest member of this family, 9-boraanthracene, was also found to react with strong dienophiles and 0 2 to form Diels-Alder adducts. During the course of this research, two stable spirocyclic boronium ions were also generated, both of which proved to be valuable starting materials for neutral boron-centred radicals.
- ItemOpen AccessCatalytic Methylaluminum Dichloride: An Efficient Method for Accelerating the Intramolecular Diels-Alder Reaction of the Furan Diene(Elsevier, 1991) Keay, Brian A.; Rogers, Christine
- ItemOpen Accesscis,cis-Spiro[4.4]nonane-1,6-diol: A New Chiral Auxiliary for the Asymmetric Diels-Alder Reaction(Elsevier, 1996) Keay, Brian A.; Nieman, James A.
- ItemOpen AccessCONJUGATE ADDITION OF (TRIMETHYLSTANNYL) COPPER REAGENTS TO a[alpha],B[beta]-ACETYLENIC N,N-DIMETHYLAMIDES. TRAPPING OF THE INTERMEDIATES WITH ELECTROPHILES(Elsevier, 1985) Keay, Brian A.; Piers, Edward; Chong, J. Michael
- ItemOpen AccessCrystal structures of 2-endo-acetyl and 2-endo-caromethoxy-1, 4-epoxy-6, 7-dimethoxy-1,2,3,4-tetrahydronaphthalenes(National Research Council Canada, 1984-06) Taylor, N. J.; Keay, Brian A.; Rodrigo, R.
- ItemOpen AccessA Desilylation and a One-Pot Desilylation-Oxidation of Aliphatic tert-Butyldimethylsilyl Ethers Using Catalytic Quantities of PdCl2(CH3CN)2(American Chemical Society, 1996) Wilson, Noel S.; Keay, Brian A.
- ItemOpen AccessDetermining Absolute Configuration by Vibrational Circular Dichroism: (+)-(1S,5S,6S)- and (-)-(1R,5R,6R)-Spiro[4.4]nonane-1,6-diol(American Chemical Society, 1995) Nieman, J. A.; Keay, Brian A.; Kubicki, M.; Yang, D.; Rauk, A.; Tsankov, D.; Wieser, H.
- ItemOpen AccessDiastereoselective diels-alder reactions with sterically hindered dienophiles for the total synthesis of (+)-dihydrodrimenin and related drimane natural products(2009) Henderson, Jeff R.; Keay, Brian A.
- ItemOpen AccessDiastereoselective intramolecular Diels-Alder reactions of the furan diene: the synthesis of (+)-1,4-epoxycadinane(National Research Council Canada, 1993-05) Rogers, Christine; Keay, Brian A.