CHED 856 |
| Mark G. Stocksdale and Zachary A. Seymour. Department of Chemistry, Earlham College, 801 National Road West, Richmond, IN 47374 |
| The focus of this study is nucleophilic substitution of cyclic β-hydroxy tertiary amines run under Mitsunobu conditions. Under these conditions cyclic β-hydroxy tertiary amines do not simply yield the expected product. Instead, a mixture of the expected product (ring size retention) as well as either a ring contracted or expanded product results. The observation of both products supports the existence of a bicyclic aziridinium ion intermediate. 1H NMR was used to analyze the reaction mixtures and determine the product molar ratios, which appear to be determined predominately by the nucleophile. Several nucleophiles were successfully used with various cyclic β-hydroxy tertiary amines. Other conditions tested included varying solvents and temperatures. Our current results and future plans for alternate experimental protocols and synthetic applications are discussed. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |
