Computational assessment of non-heteroatom-stabilized carbene complexes reactivity: Formation of oxazine derivatives
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Universidad de La Rioja
info
ISSN: 0022-3263
Year of publication: 2014
Volume: 79
Issue: 23
Pages: 11824-11828
Type: Article
More publications in: Journal of Organic Chemistry
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Abstract
A complete DFT-level mechanism elucidation of the two-step reaction of non-heteroatom-stabilized carbenes with imines, followed by addition of alkynes to yield oxazine derivatives, is presented. These compounds show different reactivity than the equivalent Fischer carbene complexes. A rationale of the experimental outcome is presented together with some suggestion for increasing the scope of the reaction, with special attention to the solvent effects in the regioselectivity.