English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

Cyclobutenes by Platinum-Catalyzed Cycloisomerization Reactions of Enynes

MPS-Authors
/persons/resource/persons58380

Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58503

Davies,  Paul W.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58588

Gress,  Tobias
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

External Resource
No external resources are shared
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)

[199]SI.pdf
(Supplementary material), 95KB

Citation

Fürstner, A., Davies, P. W., & Gress, T. (2005). Cyclobutenes by Platinum-Catalyzed Cycloisomerization Reactions of Enynes. Journal of the American Chemical Society, 127(23), 8244-8245. doi:10.1021/ja050845g.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-94F1-3
Abstract
1,6-Enynes bearing (electron-rich) aryl substituents on their alkyne moiety rearrange to cyclobutene derivatives in the presence of catalytic amounts of PtCl2 in toluene. The reaction is significantly accelerated when performed under an atmosphere of CO (1 atm), most likely by increasing the electrophilicity of the metal template by temporary coordination to this π-acidic ligand. This transformation allows the build up of considerable strain in the products as witnessed by the productive formation of tricyclic skeletons, such as 7 or 9. Moreover, these products provide evidence for the mechanistic scenario of platinum-catalyzed cycloisomerization reactions previously proposed, which are thought to proceed via organo−platinum species that mimic the reactivity of metal-complexed “nonclassical” carbocations.