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Synthesis 2012; 44(12): 1818-1824
DOI: 10.1055/s-0031-1290945
DOI: 10.1055/s-0031-1290945
special topic
Tandem Nucleophilic Addition/Fragmentation of Vinylogous Acyl Nonaflates for the Synthesis of Functionalized Alkynes, with New Mechanistic Insight
Autoren
Weitere Informationen
Publikationsverlauf
Received: 03. März 2012
Accepted: 07. März 2012
Publikationsdatum:
04. Mai 2012 (online)
Abstract
Vinylogous acyl nonaflates, like the corresponding triflates, are subject to nucleophile-triggered fragmentation as part of a tandem process for generating functionalized alkynes. Advantages to the use of nonaflates in lieu of triflates include cost and stability. Computational analysis supports a postulated fragmentation mechanism involving a closed (cyclic) transition state with concerted extrusion of lithium sulfonate.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
Included are copies of 1H, 13C, and 19F NMR spectra and Cartesian coordinates and energies for calculations.
- Supporting Information (PDF) (opens in new window)
Primary Data
- for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis
and can be cited using the following DOI:
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