Solvolysis of K-region arene oxides: substituent effects on reactions of benz [a] anthracene 5, 6-oxide

NT Nashed, SK Balani, RJ Loncharich…

Index: Nashed, Nashaat T.; Balani, Suresh K.; Loncharich, Richard J.; Sayer, Jane M.; Shipley, David Y.; Mohan, Ram S.; Whalen, Dale L.; Jerina, Donald M. Journal of the American Chemical Society, 1991 , vol. 113, # 10 p. 3910 - 3919

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Citation Number: 25

Abstract

Abstract: The solvolytic reactivity and products formed from benz [a] anthracene 5, 6-oxide (BA-0) on substitution of a methyl group at positions 1 (I-MBA-0), 4 (4-MBA-0), 7 (7-MBA-0), 11 (11-MBA-0), and 12 (I2-MBA-O), on 7, la-dimethyl substitution (7, 12-DMBA-O), and on 7- bromo substitution in 1: 9 dioxane-water and in methanol at 25" C are reported. These substitutions result in> 150-fold differences in their rates of acid-catalyzed solvolysis and ...