Studies in the oxidative ring-opening of catechols and o-benzoquinones. Lead tetraacetate versus the copper (I) chloride/pyridine/methanol system

JG Walsh, PJ Furlong, LA Byrne, DG Gilheany

Index: Walsh, James G.; Furlong, Patrick J.; Byrne, Louise A.; Gilheany, Declan G. Tetrahedron, 1999 , vol. 55, # 38 p. 11519 - 11536

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Citation Number: 16

Abstract

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.