Stereoselectivity in the Diels-Alder reaction of phenyl-and oxy-substituted o-quinodimethanes

T Durst, EC Kozma, JL Charlton

Index: Durst, Tony; Kozma, Elisabeth C.; Charlton, James L. Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 4829 - 4833

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Citation Number: 58

Abstract

Although many o-QDM precursors are kn~ wn~,~ J~ they all suffer from the problem that they are difficult to prepare, especially with a variety of substituents. One of the simplest methods for preparing o-QDM's involves the photolysis of o-methylbenzaldehyde or its derivatives to promote intramolecular H-atom abstraction (Scheme I). 3 While the starting materials are readily available and the reaction is simple, there are problems if the dienophile, added to ...