Reference

Photoreaction of tetrahalophthalonitriles with ethers

Photoreaction of tetrahalophthalonitriles with ethers. Al-Fakhri, Khalid; Pratt, Albert C. (Dep. Chem., Univ. Manchester Inst. Sci. Technol., Manchester, Engl.). J. Chem. Soc., Chem. Commun., (12), 484-5 (English) 1976.Several substances with their cas registry numbers 1953-99-7 and 61079-88-7 may be metioned in this study. CODEN: JCCCAT. DOCUMENT TYPE: Journal CA Section: 25 (Noncondensed Aromatic Compounds) Section cross-reference(s): 22 Irradn. of tetrachloro- or tetrafluorophthalonitrile in THF or Et2O gave the corresponding .alpha.-arom. ether by halogen replacement. E.g., tetrafluorophthalonitrile with THF gave I. The reaction involves electron transfer from the ether to the excited halophthalonitrile to give a radical anion-radical cation pair. Subsequent proton transfer and ether-aryl bond formation gives the intermediates II or III (R = F, Cl) which aromatize by loss of hydrogen halide. .