Synthesis of new derivatives of a representative o-quinone scaffold by reduction at the electrode

Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

“…A mechanism comprising electron transfer from the hydroquinone dianion to dichloromethane was proposed instead of simple nucleophilic displacement. Several related studies have also been reported by the same group. − …”

Synthesis of α-Functionalized Trichloromethylcarbinols

“…In one report, N -(methoxymethyl)- N ,1,1,1-tetramethylsilanecarboxamide was reacted with chloral to provide corresponding O -trimethylsilyl protected or unprotected trichlorolacamide . The electrolysis of 9,10-phenanthrenequinone in the presence of benzenediazonium tetrafluoroborate in chloroform provided 10-hydroxy-10-(trichloromethyl)­phenanthren-9­(10 H )-one in low yield . Such compounds are found to be biologically active, as β,β,β-trichlorolactamide is effective against plant growth both pre- (mustard: dicot) and postgerminative (celery, tomatoes, coleus: dicots), while isopropyl β,β,β-trichlorolactate was active against cereal grains (monocots) .…”

Electrosynthesis of Oxazol‐2(3H)‐Ones and Diaroylhydrazines from 1,2‐Dicarbonyl Compounds and Arenediazonium Salts

“…The electroreduction of quinones in DMF, acetonitrile or 1,2‐dichloroethane, under controlled potential conditions and in the presence/absence of benzenediazonium tetrafluoroborate, was described to be an interesting entry to new hydroxy carboxamides, dioxins, cyanomethylated derivatives and other useful compounds . Similarly concomitant electrochemical reduction of a representative o‐quinone scaffold, 9,10‐phenanthrenequinone, and benzenediazonium tetrafluoroborate, using other organic solvents such as chloroform, dichloromethane or chloroacetonitrile led to new coupling products by electrochemically promoted radical pathways that offered wide scope to solvents with labile C‐H bonds. When N ‐methylformamide (NMF) was used as the solvent in the simultaneous reduction of 9,10‐phenanthrenequinone (or 1,10‐phenanthroline‐5,6‐dione) and a diazonium salt, 1,3,4‐oxadiazol‐2(3 H )‐ones and dibenzo[ c,e ]azepines were surprisingly obtained (Figure a).…”