Quinones. Part 9. Stability of quinones toward water. Synthesis of a 1, 7-naphthoquinone

KH Menting, W Eichel, HLK Schmand…

Index: Menting, Karl-Hans; Eichel, Wolfgang; Riemenschneider, Klaus; Schmand, Horst L. K.; Boldt, Peter Journal of Organic Chemistry, 1983 , vol. 48, # 17 p. 2814 - 2820

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Citation Number: 22

Abstract

Calculated relative reactivities of the benzo-, naphtho-, and anthraquinones toward water (using perturbation MO theory) reflect well the sequence of stability of the known quinones. This method may be used to predict the stability of unknown quinones toward water or other nucleophiles. A 1, 7-naphthoquinone, 3, 6-di-tert-bu-tyl-&methyl-l, 7-naphthoquinone (24), is described for the first time. It is prepared in a 13-step synthesis. On the basis of PMO ...

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