Alkylation of solid sodium and lithium 2,6-dimethylphenoxide with methyl halide vapor
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.
1949 ◽
Vol 196
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pp. 540-553
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2013 ◽
Vol 17
(19)
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pp. 2119-2126
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1972 ◽
Vol 4
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pp. 153-160
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1995 ◽
Vol 16
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pp. 335-359
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1993 ◽
Vol 214
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pp. 281-289
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