Allene Synthesis via C−C Fragmentation: Method and Mechanistic Insight

Allene Synthesis via C−C Fragmentation: Method and Mechanistic Insight

A new method of allene synthesis is described. Suitably functionalized vinyl triflates undergo fragmentation to give allenes in high yield. Computational and experimental data provide a mechanistic framework for allene formation and the complementary formation of alkynes. The method is stereospecifi...

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Veröffentlicht in:Journal of the American Chemical Society 2009-09, Vol.131 (36), p.12910-12911
Hauptverfasser: Kolakowski, Robert V, Manpadi, Madhuri, Zhang, Yue, Emge, Thomas J, Williams, Lawrence J
Format: Artikel
Sprache:eng
Schlagworte:
Alkadienes - chemical synthesis
Mesylates - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:A new method of allene synthesis is described. Suitably functionalized vinyl triflates undergo fragmentation to give allenes in high yield. Computational and experimental data provide a mechanistic framework for allene formation and the complementary formation of alkynes. The method is stereospecific.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja906189h