Abstract
1,2,3-Trimethylnaphthalene (1,2,3,-Me 3N), 1,4,5-Me 3N, 1,6,7-Me 3N, 1,2,3,4-Me 4N and 1,4,6,7-Me 3N have been sulphonated with SO 3 in nitromethane and the isomer distributions of the mono- and di-sulphonic acid mixtures, obtained by reaction with 1 equivalent of SO 3 at 0° and 3 equivalents of SO 3 at 12° respectively, are reported. The sulphodeprotonation isomer distribution follows the reactivity order predicted by the localization energies, provided that steric factors are taken into account, i.e. that sulphodeprotonations peri to a methyl and sulpho group do not occur. Disulphonation of 1,4,5-Me 3N and 1,4,5,8-Me 4N leads predominantly to the 3,6- and 2,7-disulphonic acid respectively, i.e. the “non-crossed” disulphonic acids.
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