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Study of Very Reactive Tautomeric Phenol Dienones as Dienes in Diels−Alder Reactions

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posted on 19.03.2009, 00:00 by Yves L. Dory, Andrée-Lucie Roy, Pierre Soucy, Pierre Deslongchamps
Masked ortho-benzoquinones are very reactive as diene partners in Diels−Alder reactions. Careful exploration of the orbital factors that govern their surprising behavior shows that their LUMO is almost as electron demanding as that of o-benzoquinone itself. Methyl substituents at either end of their diene system influence the activation energy through modification of the reaction pathway being more or less asynchronous.

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