Journal
TETRAHEDRON
Volume 64, Issue 10, Pages 2465-2470Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.12.045
Keywords
hypervalent iodine; styrenes; PIFA; phenonium ions
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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. (C) 2007 Elsevier Ltd. All rights reserved.
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