R. Labrecque et al., ELECTROLABILE PROTECTING GROUPS FOR KETONES - THE ELECTROCHEMICAL REDUCTIVE CLEAVAGE OF 1,3-DIOXOLANES AND 1,3-DIOXANES CONTAINING NITRO ORHALO GROUPS, Electrochimica acta, 42(13-14), 1997, pp. 2089-2099
The electroreductive cleavage of 4-(4'-nitrophenyl)-1,3-dioxolanes 1,
7-nitro-1,3-benzodioxane 2 and 5-nitro-1,3-benzodioxanes 3 was studied
in aprotic medium (DMF/Et4NClO4 (0.1 M)). The voltammetric behavior o
f these compounds showed the formation of a radical anion which is rel
atively stable on the time scale of cyclic voltammetry. When the elect
roreduction of these compounds was carried out at ca. -1.5 V vs Ag/Ag (0.01 M), at the potential of the formation of the radical anion, its
cleavage did occur with the formation of the corresponding ketone. We
also investigated the electroreduction of the 4-halomethyl- and 4,5-d
ihalomethyl-1,3-dioxolanes (4 and 5). (C) 1997 Elsevier Science Ltd.