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A Semi-Quinonoid Oxidation Product of 4: 4-Diethoxydinaphthyl

Abstract

The communication from Messrs. Hughes, Hush and Mellor1 reporting a green oxidation product of tetramethyl-benzidine and the projected extension of work to related compounds renders desirable some account of our own work on the green colour instantly developed when 4: 4′ -diethoxydinaphthyl is dissolved in a large excess of concentrated sulphuric acid. The increase of intensity of absorption (measured at 660 mμ) is linear with that of concentration of the dinaphthyl until this reaches c. 310 mgm./litre. The solubility of oxygen in sulphuric acid being 33 mgm./litre2, calculation shows the green colour to arise from the action of c. 8 gm. oxygen per gm. mol. diethoxydinaphthyl. A similar result follows if selenium dioxide or nitrous acid be used to intensify the colour. We therefore attribute the structure I to the green product.

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BADDELEY, G., GRADDON, P. & KENNER, J. A Semi-Quinonoid Oxidation Product of 4: 4-Diethoxydinaphthyl. Nature 160, 187–188 (1947). https://doi.org/10.1038/160187b0

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