QUINODIMETHANE CHEMISTRY: THE GENERATION AND TRAPPING OF QUINODIMETHANES FROM SUBSTITUTED AROMATIC HYDROCARBONS WITH HIGH-POTENTIAL QUINONES

Abstract

9,10-Dimethylanthracene and 9,10-dimethyl-9,10-dihydroanthracene react with 2 and 3 moles, respectively, of tetrachloro-l,2-benzoquinone to give the same 1:1 adduct of 9,10-anthraquinodimethane with the quinone, the structure of which was proved by ozonolysis. A lower limit for the rate of adduct formation in 1,2-dichlorobenzene at 80° is 4.22 × 10−2 l mole−1 s−1. 7,12-Dimethylbenzanthraquinodimethane was generated in a similar way and the structure of the 1:1 adduct proved by ozonolysis and by mass spectrometry. The reaction of 9,10-anthraquinodimethane with a p-quinone gave a 1:2 adduct. 9-Methylanthracene reacts with high-potential quinones by hydride abstraction at the methyl group with the formation of an ether.