Cathodic reduction of α-bromopropiophenone in an aprotic medium

Stereoselective Cyclopropanation to Homoquinones from Phenacyl Carbenes Obtained through Quinone-Electrogenerated Bases

“…Unexpected similar nucleophilic substitution reaction was also observed 31 in direct electrolysis of 2′ that afforded 3,4dimethyl-2,5-diphenylfuran contrary to the expected 3,5dimethyl-2,4-diphenylfuran.…”

Oxidation and Reduction of Halogen‐containing Compounds

“…Barba and coworkers [84][85][86][87][88][89][90][91] have published a number of papers dealing with novel syntheses based on the reduction of phenacyl bromides. Electrolysis of phenacyl bromide at a mercury cathode leads to an intermediate, which reacts to give 2,4-diphenylfuran [84].…”

“…Alternatively, the electrolytically formed dimer can be converted (via refluxing in dimethylformamide) to a 3,6-diphenylpyridazine [87]. Reduction of α-bromopropiophenone at mercury gives 1,4-diphenyl-2,3-dimethylbutan-1,4-dione [88], and the reduction of phenacyl bromides provides a synthetic pathway to 4-aryl-2-methylfurans [89] and enol carbonates [90]. Finally, 3,7-diaryl-2H-imidazo[2,1-b] [1,3,4]oxadiazines can be prepared via reduction of the semicarbazones of phenacyl bromide [91].…”

Electroreduction of halogenated fumaric esters: a combined electrochemical and computational investigation

“…In the present paper, we investigated, by cyclic voltammetry and electrolysis, on mercury and glassy carbon electrodes, the reduction of gem-tri, gem-di and mono-halide ethylfumarate derivatives [ethyl 2,2,2-tribromoethylfumarate (1), ethyl 2,2-dichloroethylfumarate (2) and ethyl 2-bromoethylfumarate (3)], in comparison with the analogous halogenated alcohols [2,2,2-tribromoethanol (4), 2,2-dichloroethanol (5), 2-bromoethanol (6), and diethylfumarate (7) (Fig. 1).…”

“…Studies on compounds which contain both or similar electroactive groups have been less frequent but encouraging from the electrosynthetic point of view. The cathodic reduction of phenacyl halides [5][6][7][8][9] and phenacyl haloacetates [10,11] using a mercury electrode and aprotic medium provided an interesting route for the electrosynthesis of heterocycles such as tetrahydrofurans and coumarins, respectively. Additionally, in respect mainly to halides, a number of studies have been concerned with dissociative electron transfer (DET) [12,13], where the dissociation of the fragile bond may follow or even be concerted to the electron transfer itself.…”