The generally accepted hypothesis that the alkylation of metal phenoxides is forced to occur at the ortho-carbon in heterogeneous reactions was investigated. Methyl iodide and bromide vapor reacts with crystalline sodium and lithium 2,6-dimethylphenoxides to give ortho-carbon/oxygen alkylation ratios not unlike those obtained in sealed tube reactions with an excess of methyl iodide or with added toluene as solvent. However, an unprecedented amount of para-methylation also occurred. The implications of these and related observations in other systems are discussed.
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Curtin et al. (1969) studied this question.