Previous work in our lab had focused on the reaction of 1,2-cyclohexanedione with bromoaryl alcohols to produce dione ether starting materials (3) for an unrelated study. During this work, we observed an unusual aromatization reaction arising from the dione ether intermediate. This observation led to a study designed to determine the scope of the reaction of 1,2-cyclohexanedione with a variety of alcohols to prepare compounds of the type (4). This current work describes our efforts to determine the scope and limitations of this chemistry with a variety of diols (5) under various conditions.

Reaction of 1,2-cyclohexanedione with diols. An unexpected aromatization reaction

249th National Meeting (2015)

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