Formation of Oxazoles from Elusive Gold(I) alpha-Oxocarbenes: A Mechanistic Study

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F16%3A10326213" target="_blank" >RIV/00216208:11310/16:10326213 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/chem.201601634" target="_blank" >http://dx.doi.org/10.1002/chem.201601634</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201601634" target="_blank" >10.1002/chem.201601634</a>

Result language
angličtina
Original language name
Formation of Oxazoles from Elusive Gold(I) alpha-Oxocarbenes: A Mechanistic Study
Original language description
The gold(I) catalyzed reaction between phenylacetylene, pyridine N-oxide and acetonitrile leading, via a putative gold-alpha-oxocarbene intermediate, towards an oxazole product has been investigated. A novel mass spectrometric method called "delayed reactant labeling" is used to track consecutive and parallel reactions. It clearly shows that the intramolecular formation of a pyridine adduct of gold-alpha-oxo-carbene is in competition with the formation of the oxazole product. The reaction mechanism most probably corresponds to competition between acetonitrile and pyridine in an almost barrierless reaction with putative gold-alpha-oxocarbene within the solvent cage. The detected ionic species have been characterized by helium tagging infrared photo-dissociation spectroscopy.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
<a href="/en/project/GA14-20077S" target="_blank" >GA14-20077S: Non-heme iron catalysts: Investigation of reaction mechanisms</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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