74077-08-0Relevant academic research and scientific papers
On the regioselectivity of the PIFA-mediated bis(trifluoroacetoxylation) of styrene-type compounds
Tellitu, Imanol,Domínguez, Esther
, p. 2465 - 2470 (2008/09/19)
The addition of the hypervalent iodine reagent PIFA [phenyliodine(III) bis(trifluoroacetate)] to a series of styrene-type compounds results in the bis(trifluoroacetoxylation) of the double bond as two possible 1,2- and 1,1-regioisomers. We found that 1,1-regioisomers resulted to be unstable during chromatographic purification yielding the related arylacetaldehydes. In this paper, we show our efforts to explore the regioselectivity of this reaction, and to rationalize the results with respect to the electronic nature of the corresponding aryl ring through alternative mechanistic pathways.
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).
