Duroquinone

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Duroquinone is an organic oxidant (C6(CH3)4O2). It is related to 1,4-benzoquinone by replacement of four H centres with methyl (Me) groups. The C10O2 core of this molecule is planar with two pairs of C=O and C=C bonds.[1]

The compound is produced via nitration of durene (1,2,4,5-tetramethylbenzene) followed reduction to the diamine and then oxidation.[2]

A derived organoiron compound22-C6(CH3)4O2)Fe(CO)3 is obtained by the carbonylation of 2-butyne in the presence of iron pentacarbonyl.[3]

The molecule has been mentioned in the popular press as a component of a "nano brain".[4]

Duroquinone was observed in a degradation products generated from pyrolysis of α-Tocopheryl acetate.[5]

References

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  1. J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.Script error: No such module "CS1 identifiers".
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  3. H. W. Sternberg, R. Markby and I. Wender, "A Quinone Iron Tricarbonyl Complex and its Significance in Organic Synthesis", Journal of the American Chemical Society 1958 volume 80, pp. 1009-1010. Script error: No such module "CS1 identifiers".
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