Abstract
Hydroxyazo-ketohydrazone tautomerism of arylhydrazones of para-para-para-, para-meta-para-, and para-ortho-para-[2.2.2]cyclophane-1,2-dione 1a, 1b and 1c was studied by means of 1H-NMR spectroscopy. Except for the phenylhydrazones 4ba and 4ca of 1b and 1c, which exist as the ketohydrazone 4-H, the azo tautomer 4-A is predominant in solution, and is more favored in chloroform and benzene than in acetonitrile. A good correlation was found between the strain of the cyclophane ring and the δ-value of OH proton in 4-H.
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