ORGN 383 |
Chemistry of non-activated aziridines: Synthesis and reactivity
| Iain D. G. Watson and Andrei K. Yudin. Davenport Research Laboratories, Department of Chemistry, The University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada |
There is a great deal of interest in the reactivity of N-activated aziridines (such as N-tosyl, N-acetyl, etc) due to their ease of preparation from olefins. However, there have been comparably few reports on the chemistry of simple N-alkyl aziridines. As part of our ongoing investigations on the synthetic applications of functionalized aziridines, we have developed new methods and approaches to the synthesis, ring opening and functionalization of non-activated aziridines. We have found that ring opening reactions of non-activated aziridines with amine nucleophiles are efficiently catalyzed by tris-(pentafluorophenyl)borane leading to derivatives of trans-1,2-diamines in high yields (Scheme 1). Mechanistic investigations suggest that in situ formed [(C6F5)3B(OH2)]·H2O catalyses the ring opening through a Brønsted acid manifold. The use of metal-bound aziridine species in nitrogen transfer reactions as well as new methods of N-functionalization will be discussed. The polymerization of aziridine-containing substrates as well as their transformation into other useful structures, such as piperazines, will also be described. |
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Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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