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Intramolecular cyclization and subsequent rearrangements of alkyne-tethered N-heterocyclic carbenes |
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| Authors: | Marc CB Legault Craig S McKay Joseph MoranMatthew A Lafreniere John Paul Pezacki |
| Institution: | a National Research Council Canada, 100 Sussex Dr., Ottawa, ON, Canada K1A 0R6 b Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, ON, Canada K1N 6N5 c Biochemistry, Microbiology and Immunology, University of Ottawa, 451 Smyth Road, Ottawa, ON, Canada K1H 8M5 |
| Abstract: | Alkyne-tethered imidazole and 1,2,4-triazole-based N-heterocyclic carbene precursors have been prepared and studies of the intramolecular reactions of carbenes are performed. Products consistent with intramolecular cyclizations and subsequent rearrangements were observed. Mechanistic studies using crossover experiments showed that the products did arise from intramolecular carbene additions. The reactions are proposed to go through vinylogous diaminocarbene intermediates similar to vinylogous dialkoxycarbenes formed during Boger cycloaddition reactions. Imidazole substituted dienes were observed to be the major products of tandem cyclization and elimination reactions that were observed for imidazole-based N-heterocyclic carbenes. |
| Keywords: | N-heterocyclic carbenes Intramolecular cyclization Diels-Alder cycloaddition |
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