4957-05-5Relevant articles and documents
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
Direct electrochemical reduction of 4,4-(2,2,2-trichloroethane-1,1-diyl)bis(methoxybenzene) (methoxychlor) at carbon and silver cathodes in dimethylformamide
McGuire, Caitlyn M.,Peters, Dennis G.
, p. G44 - G49 (2018/06/29)
Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the electrochemical reduction of 4,4-(2,2,2-trichloroethane-1,1-diyl)bis(methoxybenzene), commonly known as the pesticide methoxychlor, at glassy carbon and silver cathodes in dimethylformamide (DMF) containing 0.050 M tetra-n-butylammonium tetrafluoroborate (TBABF4). Reduction of methoxychlor at both glassy carbon and silver shows four voltammetric peaks, the first three of which are associated with cleavage of carbon–chlorine bonds; the fourth peak is assigned to reduction of 4,4-(ethene-1,1-diyl)bis(methoxybenzene). Bulk electrolyses of methoxychlor at reticulated vitreous carbon and silver mesh cathodes at potentials corresponding to each of the first three voltammetric peaks were conducted; coulometric n values and product distributions (determined by means of GC and GC–MS techniques) depend on potential. In particular, two completely dechlorinated products, namely 4,4-(ethane-1,1-diyl)bis(methoxybenzene) and 4,4-(ethene-1,1-diyl)bis(methoxybenzene) have been identified and quantitated. A mechanistic scheme is proposed to account for the formation of the various products.