Multistep reversible redox systems. 48. 1, 3-Bisquinone methide cyclobutanes and related bicyclo [1.1. 0] butanes: syntheses and redox properties

W Freund, S Huenig

Index: Freund, Wolfgang; Huenig, Siegfried Journal of Organic Chemistry, 1987 , vol. 52, # 11 p. 2154 - 2161

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Citation Number: 16

Abstract

A new approach to quinone methides is presented, which starts from quinone diazides and thioketones. Together with some model compounds, 1, 3-bisquinone methide cyclobutanes 23, 25, and 37 were synthesized. Reduction with sodium transforms these quinoid compounds into bicyclo [llO] butanes with phenolate groups in the 1, 3-positions. These phenolates can be trapped as silyl ethers 40-43. After hydrolysis, reoxidation to the ...