Faculty
William J. le Noble, 1928-2023
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
Organic Chemsitry
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.
Publications
Comment on "Phantom activation volumes le Noble WJ, Asano T JOURNAL OF PHYSICAL CHEMISTRY A 105 (13): 3428-3429 APR 5 2001
Face selection in addition and elimination in sterically unbiased systems Kaselj M, Chung WS, le Noble WJ CHEMICAL REVIEWS 99 (5): 1387-1413 MAY 1999
Temperature and para-substituent effects on the face selectivity of 1,3-dipolar cycloaddition reactions of benzonitrile oxides with 5-substituted adamantane-2-thiones, N-benzyladamantyl-2-imines, and 2-methyleneadamantanes Tsai TL, Chen WC, Yu CH, le Noble WJ, Chung WS JOURNAL OF ORGANIC CHEMISTRY 64 (4): 1099-1107 FEB 19 1999
Activation and reaction volumes in solution. 3 Drljaca A, Hubbard CD, van Eldik R, Asano T, Basilevsky MV, le Noble WJ CHEMICAL REVIEWS 98 (6): 2167-2289 SEP-OCT 1998
Effect of remote substitution on face selection in addition reactions of nor- and homoadamantan-9-ones and of several analogues, Kaselj M, Gonikberg EM, le Noble WJ JOURNAL OF ORGANIC CHEMISTRY 63 (10): 3218-3223 MAY 15 1998
Effects of substituent modification on face selection in reduction, Jones CD, Kaselj M, Salvatore RN, le Noble WJ JOURNAL OF ORGANIC CHEMISTRY 63 (8): 2758-2760 APR 17 1998