Rearrangement reactions of bicyclic systems. Part II. Rearrangements of 1-dimethylamino-5,6,7,8-tetrahalogeno-1,4-dihydro-1,4-ethenonaphthalene derivatives and the analogous 5,6,7,8-tetrafluoro-1,4-dihydro-N-methyl-1,4-iminonaphthalene in aqueous solutions
Abstract
The title compounds rearrange to biaryl derivatives in high yields in protic media. The isolation of ketonic derivatives when aromatisation is blocked shows that the driving force for the rearrangement is not provided predominantly by the aromatisation step. Evidence for an ionic mechanism is adduced from deuterium-incorporation studies.