Letter

F8BINOL, an Electronically Perturbed Version of BINOL with Remarkable Configurational Stability

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada
Org. Lett., 2000, 2 (1), pp 41–44
DOI: 10.1021/ol991244v
Publication Date (Web): December 18, 1999
Copyright © 2000 American Chemical Society

Abstract

Abstract Image

Substitution of hydrogens by fluorines at the 5, 5‘, 6, 6‘, 7, 7‘, 8, and 8‘ positions of BINOL strongly affects distribution of electron density within the biaryl skeleton but has a very small influence on the torsion angle. The most important consequence of this structural alteration is the dramatic increase in configurational stability of homochiral F8BINOL.

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Article Views: 840 Times
Received 11 November 1999
Published online 18 December 1999
Published in print 1 January 2000
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