Collect. Czech. Chem. Commun. 2008, 73, 1764-1776

Octafluoro[2.2]paracyclophane (AF4) Quinone

Wei Xu, William R. Dolbier, Jr.*, Jian-Xin Duan, Yian Zhai, Katsu Ogawa, Merle A. Battiste and Ion Ghiviriga

Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


Octafluoro[2.2]paracyclophane (AF4) has been oxidized by treatment with HIO3 in CF3CO2H to form the corresponding p-quinone along with a unique triketone. This quinone undergoes reduction to the respective hydroquinone as well as a Diels-Alder reaction with 1,3-cyclohexadiene. Its reduction potential was obtained by cyclic voltammetry and is discussed in the context of other quinones.

Keywords: Cyclophane; Fluorinated compounds; Oxidations; [2.2]Paracyclophane; Quinones; Cyclic voltammetry; UV spectra; Diels–Alder reaction.

References: 17 live references.