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Synlett 1997; 1997(1): 44-46
DOI: 10.1055/s-1997-700
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The Design of Inner-Functionalised U-Shaped Cavity Molecules: Role of Phenyl Substituents at the 1,3-Position of Isobenzofurans and Oxa-Bridges in the Dienophile as Stereochemical Controlling Elements

Ronald N. Warrener1 , Shudong Wang2 , Douglas N. Butler2 , Richard A. Russell3
  • 1Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia, Fax +61 70 30 9917; email r.warrener@cqu.edu.au
  • 2Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia
  • 3School of Biological and Chemical Sciences, Deakin University, Geelong, Victoria 3217, Australia
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Publication History

Publication Date:
22 March 2004 (online)

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1,3-Diphenylisobenzofuran reacts with fused mono- and bis-norbornenes, 7-oxanorbornenes and cyclobutene-1,2-diesters with high stereospecifity whereas the corresponding isobenzofuran cycloadditions produce mixtures; this provides a basis for regulating geometry in the construction of polyalicyclic nanostructures.

isobenzofurans - [4π+2π] cycloadditions - nanostructures - ring-strained dienophiles - bridged ethers