DOI | Resolve DOI: https://doi.org/10.1016/j.tetlet.2012.08.038 |
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Author | Search for: Legault, Marc C.B.1; Search for: Mckay, Craig S.1; Search for: Moran, Joseph1; Search for: Lafreniere, Matthew A.1; Search for: Pezacki, John paul1 |
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Affiliation | - National Research Council of Canada. Medical Devices
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Format | Text, Article |
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Subject | N-heterocyclic carbenes; Intramolecular cyclization; Diels–Alder cycloaddition |
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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. |
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Publication date | 2012-10 |
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In | |
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Language | English |
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Peer reviewed | Yes |
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Identifier | S0040403912013974 |
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NPARC number | 21268743 |
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Export citation | Export as RIS |
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Report a correction | Report a correction (opens in a new tab) |
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Record identifier | 332a1863-5527-4e37-ad03-6e454a58fc74 |
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Record created | 2013-11-12 |
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Record modified | 2020-04-21 |
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