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Main Title Synthesis of New Cyclopenta-Fused PAH (Polycyclic Aromatic Hydrocarbons) Isomers of Cata-Annelated Benzenoid Systems (Journal Version).
Author Sangaiah, R. ; Gold, A. ;
CORP Author North Carolina Univ. at Chapel Hill. School of Public Health.;Health Effects Research Lab., Research Triangle Park, NC.
Publisher c1987
Year Published 1987
Report Number EPA-R-811817; EPA/600/J-87/387;
Stock Number PB89-101125
Additional Subjects Aromatic polycyclic hydrocarbons ; Chemical reactions ; Reprints ; Benzaceanthrylene ; Benzacephenanthrylene ; CAS 19770-52-6 ; CAS 16683-64-0 ; CAS 216-48-8
Library Call Number Additional Info Location Last
NTIS  PB89-101125 Some EPA libraries have a fiche copy filed under the call number shown. 07/26/2022
Collation 8p
The syntheses of three new benz-annelated derivatives of aceanthrylene and acephenanthrylene are reported. These systems are of interest in studies on mechanisms of bioactivation and structure-activity correlations because of their predicted high level of biological activity. Of the three isomers, benz(d)aceanthrylene has been synthesized by two routes involving Friedel-Crafts acylations of 1,2,3,4-tetrahydronaphthacene with chloroacetyl chloride or oxalyl chloride as the key step. The cyclic ketone product from each route has been successfully elaborated. Synthesis of benz(k)aceanthrylene involves preparation of acenaphthene-3,4-di-carboxylic anthdride and its smooth conversion. A straightforward and high-yield synthesis of benz(j)acephenanthrylene is described utilizing a Robinson annelation reaction of methyl vinyl ketone with a previously reported ketonic precursor of acephenanthrylene. (Copyright (c) 1987 American Chemical Society.)