Reactions of 5,6-chrysenequinodimethane

Abstract

The 5,6-dihydro-5,6-dimethylchrysene-5,6-diol obtained from 5,6-chrysenequinone and methylmagnesium iodide is shown to be a trans-racemic form. The diol can be thermally dehydrate to give 5,6-chrysenequinodimethane; Diels–Alder reaction of this with maleic anhydride and with 1,4-naphthaquinone gives derivatives of benzo[g]-chrysene and benzo[c]naphtho[1,2-a]naphthacene, respectively, from which the parent hydrocarbons have been obtained.

The reaction of the diol with methanolic hydrogen chloride at 0° has been studied; it gives 6-chloromethyl-5-methylchrysene and 12-chloro-5,6-dimethylchrysene. The mechanism of this reaction and the proton magnetic resonance spectra of several chrysene derivatives are discussed.