The electrochemical reduction of 1,2-bis(bromomethyl)benzene (1a) has been investigated in the presence of naphthoquinone derivatives (2a-c) in EtOH/LiClO4 solution using cyclic voltammetry (CV) and constant-current electrolysis. The voltammetric results indicate that an electro-reductive Diels-Alder type sequential reaction occurs between 2a-c and cathodically generated o-quinodimethane (1b) to produce 3a-c as final products. The mechanism of the electrochemical reaction is proved as an electron transfer-chemical reaction (EC) pathway using the constant-current electrolysis (C) 2015 Elsevier B.V. All rights reserved.