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Synlett 1997; 1997(2): 196-198
DOI: 10.1055/s-1997-738
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The 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Coupling of Norbornenes and 7-Oxanorbornenes under High Pressure: New Structures, Mechanistic Detail and Synthetic Applications

Ronald N. Warrener1 , Davor Margetic2 , Edward R.T. Tiekink3 , Richard A. Russell4
  • 1Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia, Fax: +61 79 30 9917, E-mail: r.warrener@cqu.edu.au
  • 2Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia
  • 3Department of Chemistry, University of Adelaide, Adelaide, South Australia, 5005, Australia
  • 4Department of Biological and Chemical Sciences, Deakin University, Geelong, Victoria, 3217, Australia
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Publication History

Publication Date:
31 December 2000 (online)

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A comparison of reactivities, site selectivities, calculation and thermal versus high pressure (14 kbar) reaction conditions are used in a study of the coupling of bicyclic alkenes with 1,3,4-oxadiazoles (and 1,3,4-thiadiazoles) which sets the boundary conditions for such coupling and identifies a 1,3-dipolar species as the likely intermediate.

high pressure - cycloaddition - AM1 calculations - mechanism - polyalicyclics