Abstract
(Chemical Equation Presented) A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclopropane- cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/ reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.
Original language | English (US) |
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Pages (from-to) | 7822-7833 |
Number of pages | 12 |
Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 20 |
DOIs | |
State | Published - Oct 16 2009 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry