EPR and ENDOR Studies of 6-Substituted Benzopyrene Cation Radicals
The EPR spectrum of 6-methylbenzopyrene (6-CH3-BaP) in thallium(III)tris(trifluoroacetate)-trifluoroacetic acid (TTFA/TFA) solutions has been analyzed in terms of the 6-CH3-BaP cation radical with the aid of the ENDOR spectrum.Benzopyren (BaP) in TTFA/TFA gives an EPR and ENDOR spectra which are assigned and analyzed as the 6-(trifluoroacetoxy)benzopyrene cation radical.The EPR of several other 6-substituted BaP's have been investigated in both H2SO4 and TTFA/TFA solutions.Reactions of 6-CH3-BaP and 6-F-BaP in H2SO4 were observed.The EPR spectrum of 6-CH3-BaP(+.) changes over a period of an hour into the spectrum identical with that of 6-CH2OH-BaP(+.).Similarly, the EPR spectrum of 6-F-BaP(+.) in H2SO4 changes to one identical with 6-OH-BaP(+.).These observations are discussed in terms of their possible significance to the metabolic reactions of these compounds.
Sullivan, Paul D.,Ocasio, Ignacio J.,Chen, Xinhua,Bannoura, Fouad
Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene
Photolabile 6-nitrobenzo[a]pyrene (6-nitroBaP) released nitric oxide (NO) under visible-light irradiation. The generation of NO and the concomitant formation of the 6-oxyBaP radical were confirmed by ESR. BaP quinones were also detected as further oxidize
Fukuhara,Kurihara,Miyata
p. 8662 - 8666
(2007/10/03)
PREPARATION, PROPERTIES, AND SOME CHEMICAL REACTIONS OF PHENALENOFURAN
The synthesis of hitherto unknown phenalenofuran (1), in 11 percent overall yield from 2-naphthol, has been achieved.Its (1)H and (13)C n.m.r. spectra have been fully assigned by means of heteronuclear 2D correlations.The furanoid moiety of (1) displays Diels-Alder diene reactivity in its reactions with benzyne, dimethyl acetylenedicarboxylate, and singlet oxygen.The furan ring of (1) also suffers oxidation by m-chloroperbenzoic acid and undergoes catalytic hydrogenation.This chemistry appears to be more characteristic of naphthofuran than of naphthofuran although both structural units co-exist in structure (1).
Weeratunga, Gamini,Austrup, Mona,Rodrigo, Russell
p. 3169 - 3174
(2007/10/02)
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