82120-25-0Relevant academic research and scientific papers
Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents
Wu, Anhui,Duan, Yazhen,Xu, Daiwang,Penning, Trevor M.,Harvey, Ronald G.
experimental part, p. 2111 - 2118 (2010/04/26)
The hypervalent iodine reagents o-iodoxybenzoic acid (IBX) and bis(trifluoro-acetoxy)iodobenzene (BTI) are shown to be general reagents for regio-controlled oxidation of polycyclic aromatic phenols (PAPs) to specific isomers (ortho, para, or remote) of polycyclic aromatic quinones (PAQs). The oxidations of a series of PAPs with IBX take place under mild conditions to furnish the corresponding ortho-PAQs. In contrast, oxidations of the same series of PAPs with BTI exhibit variable regiospecificity, affording para-PAQs where structurally feasible and ortho-PAQs or remote PAQ isomers in other cases. The structures of the specific PAQ isomers formed are predictable on the basis of the inherent regioselectivities of the hypervalent iodine reagents in combination with the structural requirements of the phenol precursors. IBX and BTI are recommended as the preferred reagents for regio-controlled oxidation of PAPs to PAQs.
Synthesis of phenol and quinone metabolites of benzo[a]pyrene, a carcinogenic component of tobacco smoke implicated in lung cancer
Xu, Daiwang,Penning, Trevor M.,Blair, Ian A.,Harvey, Ronald G.
experimental part, p. 597 - 604 (2009/06/20)
Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental pollutants produced in the combustion of organic matter. PAHs are present in automobile exhaust and tobacco smoke, and they have recently been designated as human carcinogens. Current ev
SYNTHESIS OF NON-K-REGION ORTHO-QUINONES OF POLYCYCLIC AROMATIC HYDROCARBONS FROM CYCLIC KETONES
Platt, Karl L.,Oesch, Franz
, p. 163 - 166 (2007/10/02)
Non-K-region o-quinones of polycyclic aromatic hydrocarbons are prepared in four steps from cyclic ketones via dehydrogenation of tetrahydrodiols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone.
