Regiochemistry of the coupling of aryl radicals with nucleophiles derived from the naphthyl system. Experimental and theoretical studies

AB Pierini, MT Baumgartner…

Index: Pierini, Adriana B.; Baumgartner, Maria T.; Rossi, Roberto A. Journal of Organic Chemistry, 1991 , vol. 56, # 2 p. 580 - 586

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Citation Number: 27

Abstract

Conclusions Based on these calculations, the C3H2F3+ system should be ideal for observing fluorine migrations. It is predicted that the relatively unstable 3, 3, 3-trifluoro-2- propenyl cation 3 can readily rearrange to either the 1, 1, 2-trifluoroallyl cation 4 or the 1, 1, 3- trifluoroallyl cation 16. By analogy, rearrangement via 1, 2-or 1, 3-fluorine shifta to allyl cations should be favorable in the system CF3CH= C+ CF3 as well. Efforts to observe ...