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EPR Study of the Thermal Decomposition of Transannular Peroxide of Anthracene

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DOI: 10.4236/ijoc.2011.12007    4,094 Downloads   8,864 Views

ABSTRACT

Thermal decomposition of transannular peroxide of anthracene (POA) (or 9,10-epidioxido anthracene) was studied by means of electron paramagnetic resonance spectroscopy (EPR) in the solid as well as in the liquid phases. Decomposition process proceeds via cleavage of the O-O bridge of the POA molecule, generating thus an alcoxy intermediate radical. Its concentration increases to a certain equilibrium stage during the time scale of the experiment. EPR spectra in the solid state were of the singlet type at the temperatures over 350 K, a doublet like anisotropic spectra were measured at the room temperature, both having g-value 2.0033. EPR spectrum from POA decomposed in benzene indicates four protons with higher (2aH = 0.305 mT, 2aH = 0.335 mT) and four protons with a lower (2aH = 0.075 mT, 2aH = 0.105 mT) splitting constants, corresponding well the radical expected after cleavage of O-O bridge.

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L. Lapčík, B. Lapčíková and A. Staško, "EPR Study of the Thermal Decomposition of Transannular Peroxide of Anthracene," International Journal of Organic Chemistry, Vol. 1 No. 2, 2011, pp. 37-40. doi: 10.4236/ijoc.2011.12007.

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