Studies in the Oxidative Ring-Opening of Catechols and o-Benzoquinones. Lead Tetraacetate versus the Copper(I) Chloride/Pyridine/Methanol System

摘要

Lead tetraacetate oxidative ring-opening of a series of substituted catechols provides the corresponding substituted cis,cis-2,4-diene-1,6-dioates (1-10) in fair to good yields. A number of improvements on Wiessler's procedure for this reaction are reported. The analogous copper(I) chloride/pyridine/methanol ring-opening was found to be ineffective as a general synthetic method for this transformation.