ipso Nitration. XXIV. Nitration of 2-methylphenols. Formation and rearrangement of 6-methyl-6-nitrocyclohexa-2, 4-dienones

GG Cross, A Fischer, GN Henderson…

文献索引：Cross, Gordon G.; Fischer, Alfred; Henderson, George N.; Smyth, Trevor A. Canadian Journal of Chemistry, 1984 , vol. 62, p. 1446 - 1451

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被引用次数: 24

摘要

Nitration of o-cresol and some mono-, di-, and trimethyl derivatives in acetic anhydride at- 60° C gives 6-methyl-6-nitrocyclohexa-2, 4-dienones. The dienones are more labile than the isomeric 4-methyl-4-nitrocyclohexa-2, 5-dienones and, if the 2-position of the dienone is not blocked, undergo regiospecific rearrangement to 6-nitro-o-cresols. 2, 3, 6-Trimethyl-and 2, 3, 5, 6-tetramethylphenol also give a 2, 5-dienone with nitro attached to a secondary carbon.

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