Tetrahedron p. 3523 - 3532 (1987)
Update date:2022-08-03
Topics:
Deya, Pedro M.
Dopico, Mercedes
Raso, Angel Garcia
Morey, Jeronimo
Saa, Jose M.
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 of Fremy's salt, thus eventually providing the corresponding p-quinones".A similar rule for the ortho vs. ortho' regioselectivity could not be so precisely formulated since now steric effects play a significant major role.
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