ORGN 137 |
| Biaryl molecules with resolvable enantiomeric atropisomers, particularly 1,1'-binaphthyl derivatives such as BINOL and BINAP, have found a myriad of useful applications in asymmetric synthesis. Pursuant of biaryl compounds which offer novel ambifunctional properties, we have prepared a new atropisomeric chiral entity based on the rarely investigated 8,8'-biquinolyl framework, 7,7'-dihydroxy-8,8'-biquinolyl (1). The 8,8'-biquinolyl moiety is a heteroanalog of the better known 1,1'-binaphthyl system in which the peri C-H bonds have been formally replaced with sp2 hybridized nitrogen atom lone pairs. The preparation, physical characterization, and resolution of 1 will be described together with preliminary results concerning the configurational stability and chemical reactivity of this intriguing compound.
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
