Evidence against 1,2-Migrations in Aryl Cations

Article abstract of DOI:10.1021/jo00175a014

Photolytic methoxydediazoniation of 2-diazo-4-methylphenol (1) and 2-diazo-5-methylphenol (2) in 50percent CH3OH-H2SO4 yielded 2-methoxy-4-methylphenol (creosol) and 2-methoxy-5-methylphenol (isocreosol), respectively.The absence of detectable amounts of crossover products (within the limits of detection of 5percent) in both reactions demonstrates that no 1,2-hydroxyl shift occured in the intermediate phenylium ion nor could the hypothetical protonated benzoxirene be an intermediate in this reaction.