Electroreduction of organic compounds. 31. Electroreduction of 2- and 3-Chlorodibenzofuran in Deuterated Methanol
作者:J�rgen Voss、Edgar Waller、Petra Kr�nke
DOI:10.1002/prac.19983400505
日期:——
The cathodic reduction of dibenzofuran (2), 2-chlorodibenzofuran (4), and 3-chlorodibenzofuran (1) in deuterated methanol is investigated. The Bh-ch-type reduction product 1,4-dibenzofuran (3) is formed from 1 via 2, whereas 2-chloro-1,4-dihydrodibenzofuran (5) is obtained as by-product besides 3 from 4 as starting compound. Deuterium is only incorporated into the reduction products if CH,OD or CD,OD but not if CD,OH are used. This observation is strongly indicative of a polar mechanism involving protonation rather than a radical mechanism with hydrogen atom abstraction to be operative.
Belkasmioui, Ahmed; Simonet, Jacques, Bulletin de la Societe Chimique de France, 1989, # 5, p. 699 - 702