74077-04-6Relevant articles and documents
Oxidation of Alkenes by Iodine Tris(trifluoroacetate). On the cis-Effect of the Trifluoroacetate Group in Oxidations
Buddrus, Joachim,Plettenberg, Horst
, p. 1494 - 1506 (2007/10/02)
Iodine tris(trifluoroacetate) oxidizes alkenes to α-glycol bis(trifluoroacetates) (eq. (1) and tab. 1).By-products are acylals emerging out of a 1,2-shift (eq. (3)). 1,2-Disubstituted alkenes are mainly transformed into cis-glycol derivatives and tri- and tetrasubstituted alkenes to cis/trans mixtures.The oxidations proceed via 2-acyloxy-1,3-dioxolanes, formerly postulated by Winstein et al. as intermediates in similar oxidations, but only now isolated (comp. 3) and examined by NMR and rearranged to the corresponding α-glycols (3 -> 5).A similar reaction course isproposed for certain other alkene oxidations known from literature, in which a trifluoroacetate group is involved and which proceed under cis-addition (table 3).