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 ...