ORGN 584 |
Synthesis, characterization, and elaboration of endo[n.n.n.n] (n = 3 or 4) metacyclophanes
| Dennis H. Burns, Charles L. Jayne, and Sumith A. Kularatne. Department of Chemistry, Wichita State University, 1845 Fairmount, Wichita, KS 67260-0051 |
| The systhesis of [n.n.n.n] metacyclophanes (n=1 i.e. calix[4]arene) has been an item of importance to supermolecular chemistry. But there are few examples of devices created from calix[n]arenes (n>4) with a larger annulus. With this increase in phenolic rings, there is an associated difficulty with regiochemical control in the chemical modification of the macrocycle’s rims. The direction we have taken is to increase the size of the annulus, and attempt to keep conformations at a minimum, by increasing the number of bridging methylene units connecting the four aromatic rings. An improved synthetic pathway is presented which entails a protection-deprotection format arranged around a Grignard reaction taking a total of six steps with our copper catalyst playing a key role. 
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Heterocycles, Aromatics, Metal-Mediated Reactions, Physical Organic, Materials
9:00 AM-11:00 AM, Wednesday, March 26, 2003 Convention Center -- Hall I-1, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 24, 2003 Convention Center -- Hall G, Sci-Mix
Division of Organic Chemistry
The 225th ACS National Meeting, New Orleans, LA, March 23-27, 2003
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