By Ronald G. Harvey (auth.), Dr. Alasdair H. Neilson (eds.)
The volumes 3/I (Chemistry) and 3/J (Biology) current various facets of the environmental chemistry and ecology of PAHs and similar compounds. Emphasis has been put on a variety of facets now not typically coated in different shows. They hide not just easy facets of the chemistry, research, assets, physico-chemical determinants of environmental distribution, and dissemination of PAHs, but additionally very important components corresponding to heteroarenes, and PAHs made from certainly happening alicyclic precursors. Atmospheric degradation and transformation of PAHs are mentioned in addition to microbial metabolism of either PAHs and heteroarenes. traditional and critical new features of mammalian metabolism and the induction of melanoma are provided, and the techniques used for demonstrating the constitution of adducts concerning PAH metabolites are mentioned in detail.
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Additional resources for PAHs and Related Compounds: Chemistry
Dienophiles fail to react with PAHs, such as triphenylene and chrysene, reaction of which would not result in a gain in sextets,. For susceptible PAHs, the preferred molecular site of attack is that which affords the product with the maximum number of sextets [9,10,198]. For example, addition of maleic anhydride to benzo[a]naphthacene takes place regioselectively at the 8,13-positions with a net gain of one sextet. Addition at the 7,14-positions is not favorable, since it results in no increase in sextets.
Arylketone and aldehyde products are obtained in good yields. The mechanism is believed to involve initial formation of a benzylic carbocation which is trapped by water or acetic acid followed by a second hydride abstraction at the benzylic carbon site to yield the products. Where more than one benzylic site is present, oxidative attack occurs preferentially at the site which affords the most stable carbocation intermediate, predictable from the calculated fJ-delocalization energies. For example, oxidation of 11-methyl-6,7, 16, 17-tetrahydro-15H-cyclopenta [a] phenanthrene takes place regiospecifically in the 17-position, one of five benzylic sites, to provide the 17-keto derivative, a precursor of an important environmental carcinogen [184,197].
Photodimerization of phenanthrene derivatives follows a different course, affording 2 + 2 cycloadducts (6) [13,122]. These reactions generally take place regiospecifically to yield syn "head-to-tail" dimers in which the polycyclic aromatic rings are face to face. Acenaphthylene and other PARs having an unsaturated five-membered ring also photodimerize to afford 2 + 2 cycloadducts . Sensitized photodimerization of aceanthrylene provides a mixture of the syn and anti head-to-head (7 and 8) and headto-tail stereoisomers (not shown) .
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