Diene-substituent effects on the rate of the retro-Diels-Alder reaction. Cycloreversion reactivity varying over a range of 105

…, BF Duerr, P Nanjappan, AW Czarnik

Index: Chung, Y.-S.; Duerr, Brook F.; Nanjappan, P.; Czarnik, Anthony W. Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1334 - 1336

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Citation Number: 19

Abstract

Summary: The retro-Diels-Alder reaction of anthracene cycloadducts is influenced by diene substituents in the following ways:(1) electron-donating groups increase the reaction rate, and the accelerating effect is subject to geometric modulation;(2) electron-withdrawing groups may decrease or increase the reaction rate, although the effect is rarely large; and (3) steric acceleration is relatively small and demonstrates an unprecedented bell-shaped ...