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William J. le Noble Professor Emeritus B.S., 1949, Chemical Engineering, Advanced Technical School, Dordrecht, the Netherlands; Ph.D., 1957, University of Chicago; Postdoctoral Research Associate, 1958, Purdue University; author, "Highlights of Organic Chemistry;" Senior Editor, Journal of Organic Chemistry, 1978-1989. (631) 632-7950 Email: wlenoble@notes.cc.sunysb.edu Publications |
| ORGANIC CHEMISTRY Our research in stereochemistry is concerned with electronic control of face selection. Whenever in an organic reaction a group or atom is added to a trigonal carbon atom and conversely, one is eliminated from a tetragonal atom, nature must decide at which face this addition or elimination will occur. Past studies of the factors controlling the outcome have been complicated and rendered uncertain by the fact that the probes used generally had sufficient conformational freedom to leave the results in doubt; however, steric effects clearly do influence them. To see the electronic factor, it is necessary not only to freeze out conformational flexibility but also to render the two faces sterically equivalent. The probes used in our studies, 5-substituted 2-adamantylidene derivatives, have this unique combination of qualities. |
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