ORGN 672 |
Dearomatization of pyrroles: Reaction of a fused 1,2-diacylpyrrole with organometallic reagents and rearrangement of the products
| Anil R. Ekkati and Dallas K. Bates. Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931 |
| Pyrrolyl carbinol (2-hydroxymethylpyrrole) derivatives are important intermediates in organic chemistry, particularly in the coupling reactions used for porphyrin synthesis. The two major routes to these carbinols involve either acid-catalyzed condensation of pyrroles with aldehydes and ketones or the (less studied) addition of organometallic reagents to 2-pyrrole carbaldehyde or ketone derivatives. We have studied addition of various hydride reducing agents, Grignard reagents and organolithiums to the fused 1,2-diacylpyrrole 1. The regiochemistry of additions as well as novel Cα /C5 molecular rearrangements and oxidation processes of the products will be presented. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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