ORGN 399 |
| The novel heptachloro-1'-methyl-1,2'-bipyrrole (“Q1”) (1) is a natural organohalogen that has been detected in more than 100 worldwide environmental samples. It is found in Antarctic air, fish, seabird eggs, marine mammals, and Eskimo women's milk. In recent years mixed halogenated 1,2'-bipyrroles have also been detected in several marine sources. For example, heptabromo-1'-methyl-1,2'-bipyrrole (2) was reported in 2006, but this structure has remained unconfirmed until the present work. We now report relatively efficient syntheses of both Q1 and heptabromo-1'-methyl-1,2'-bipyrrole and the isomeric heptabromo-1'-methyl-1,3'-bipyrrole in two steps from 2- and 3-nitropyrroles. Our syntheses provide facile access for the first time to these remarkable “PCB-like” polyhalogenated natural products.
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Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster
Division of Organic Chemistry |
