Duroquinone Explained
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.
A derived organoiron compound (η2,η2-C6(CH3)4O2)Fe(CO)3 is obtained by the carbonylation of 2-butyne in the presence of iron pentacarbonyl.[2]
The molecule has been mentioned in the popular press as a component of a "nano brain".[3]
Duroquinone was observed in a degradation products generated from pyrolysis of α-Tocopheryl acetate.[4]
Notes and References
- 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.
- 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.
-
- Wu . Dan . O’Shea . Donal F. . 2020-03-24 . Potential for release of pulmonary toxic ketene from vaping pyrolysis of vitamin E acetate . Proceedings of the National Academy of Sciences . en . 117 . 12 . 6349–6355 . 10.1073/pnas.1920925117 . 0027-8424 . 7104367 . 32156732. free .
