The reaction of certain phenyl nitronyl nitroxide derivatives with strong acceptors such as TCNQF4 or TCNQ in appropriate solvents give the corresponding imine nitroxide derivatives by an anomalous deoxygenation reaction with acceptors in a selective manner.
References
1.
For example, Synthetic Chemistry of Stable Nitroxides, eds. VolodarskyL. B., ReznikovV. A., and OvcharenkoV. I., CRC Press, Boca Raton, FL, 1994, and references cited therein.
2.
UllmanE. F., CallL., and OsieckiJ. H., J. Org. Chem., 1970, 35, 3623.
MelbyL. R., HarderR. J., MahlerW. R., BensonR. E., and MochelW. E., J. Am. Chem. Soc., 1962, 84, 3374; R. C. Wheland and E. L. Martin, J. Org. Chem., 1975, 40, 3101.
7.
For example, NakatsujiS., and AnzaiH., J. Mater. Chem., 1997, 7, 2161 and references therein.
For the biological significance of nitroxide radicals see, for example, GriffithO. H., and WaggonerA. S., Acc. Chem. Res., 1969, 2, 17; H. M. McConnell and B. G. Mcfarland, Quart. Rev. Biophys., 1970, 3, 91.
10.
UllmanE. F., OsieckiJ. H., BoocockD. G. B., and DarcyR., J. Am. Chem. Soc., 1972, 94, 7049.
