Organotin Hydride Reduction of Benzyl Bromides
Organometallics2002Vol. 21(14), pp. 3066–3068
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Lawrence W. Menapace, Matthew B. Loewenthal, Jeremy F. Koscielecki, Lucas Tucker, Linda C. Passaro, Rosa Montalbano, Anthony J. Frank, Joseph Marrantino, Jeanette Brunner
Abstract
A Hammett study was carried out on the tributyltin hydride reduction of substituted benzyl bromides. Electron-withdrawing groups facilitate the reaction, whereas electron-releasing groups have little or no impact on the rate. This unusual effect creates a discontinuity in the Hammett plot. Electron-withdrawing groups stabilize both the free radical and polar character of the transition state. Electron-releasing groups, however, stabilize the free radical character but destabilize the polar character of the transition state.
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