Intramolecular cyclization and subsequent rearrangements of alkyne-tethered N-heterocyclic carbenes

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DOIResolve DOI: http://doi.org/10.1016/j.tetlet.2012.08.038
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TypeArticle
Journal titleTetrahedron Letters
ISSN00404039
Volume53
Issue42
Pages56635666; # of pages: 4
SubjectN-heterocyclic carbenes; Intramolecular cyclization; Diels–Alder cycloaddition
AbstractAlkyne-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.
Publication date
LanguageEnglish
AffiliationMedical Devices; National Research Council Canada
Peer reviewedYes
IdentifierS0040403912013974
NPARC number21268743
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Record identifier332a1863-5527-4e37-ad03-6e454a58fc74
Record created2013-11-12
Record modified2016-05-09
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