Tetrahedron

On the regioselectivity of the fremy's salt oxidation of phenols

PM Deya, M Dopico, AGRJ Morey, JM Saa

文献索引：Deya, Pedro M.; Dopico, Mercedes; Raso, Angel Garcia; Morey, Jeronimo; Saa, Jose M. Tetrahedron, 1987 , vol. 43, # 15 p. 3523 - 3532

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被引用次数: 27

摘要

A detailed study of the regioselectivity of the Fremy's salt oxidation of phenols, including a series of MNDO calculations of the intermediate phenoxy radicals, has been carried out. The analysis of these results has led us to establish a new rule for the para vs. ortho regioselectivity, namely:“C-4 unsubstituted phenols, as well as phenols substituted at C-4 with easy-to-displace groups, undergo oxidation (or oxidative degradation) by the action ...