Calculated relative reactivities of the benzo-, naphtho-, and anthraquinones toward water (using perturbation MO theory) reflect well the sequence of stability of the known quiñones. This method may be used to predict the stability of unknown quiñones toward water or other nucleophiles. A 1,7-naphthoquinone, 3,6-di-tert-butyl-8-methyl-l,7-naphthoquinone (24), is described for the first time. It is prepared in a 13-step synthesis. On the basis of PMO calculations and analogous cases the alkyl groups in 24 were considered to be adequate to shield the 1,7-naphthoquinoid system from attack of water and dimerization. 24 shows an unexpected low stability. According to MNDO calculations the alkyl groups cause a high steric strain in the molecule, possibly responsible for the observed low stability.

Die Stabilität zahlreicher Chinone gegenüber der Einwirkung von Wasser wird untersucht.