The Journal of Organic Chemistry

Mechanism of the Gibbs Reaction. 3. Indophenol Formation via Radical Electrophilic Aromatic Substitution (SREAr) on Phenols

I Pallagi, A Toro, O Farkas

Index: Pallagi, Istvan; Toro, Andras; Farkas, Oedoen Journal of Organic Chemistry, 1994 , vol. 59, # 22 p. 6543 - 6557

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Citation Number: 8

Abstract

Different products are formed, depending on the para substituent (R) when 2, 6- dichlorobenzoquinone N-chloroimine (lb) reacts with the anion of the 4-substituted phenol (2). If the group R can leave as a cation (ie, R is an electrofugal leaving group) such as H, CHzNMez, CHzOH, etc., then the reaction yields indophenol (3), the normal Gibbs product. If the group R cannot leave as a cation such as CH3, the final product of the reaction will be ...