Journal of Chemical Crystallography

, Volume 40, Issue 1, pp 76–79 | Cite as

Synthesis and Structures of Two Functionalized Isobenzofurans: (3aR,7aR,4S,5S)-1,3,3a,4,5,7a-Hexahydro-5-methyl-3-oxoisobenzofuran-4-carboxylic acid and (3aα,4β,7β,7aα)-4-[(Acetyloxy)methyl]-3a,4,7,7a-tetrahydro-7-methyl-1,3-isobenzofurandione

  • George D. Bennett
  • Lauren R. Bringman
  • Elise M. Wildman
  • Kraig A. Wheeler


The title compounds, C10H12O4 and C12H14O5, were prepared as part of an ongoing study to explore the practical aspects of solventless reaction methods. As confirmed by the crystal structures, treatment of maleic anhydride with (2E,4E)-hexa-2,4-dien-1-ol or its acetate counterpart resulted in cis bicyclo [4.3.0] molecular frameworks. The racemic product derived from the dienol synthon crystallized in chiral space group P212121 via a pasteurian resolution process with molecules organized by carboxyl⋯carboxyl and C–H⋯O contacts. The acetate derivative crystallizes in space group Cc.

Graphical Abstract

The synthesis and crystal structures of the title compounds, C10H12O4 and C12H14O5, are reported.


Crystal structure Hydrogen bonds Isobenzofuran Bicyclo Green chemistry Diels–Alder 



The authors acknowledge National Science Foundation (0722547 and DUE-9952602) for support of this crystallographic investigation. High field NMR spectra were provided by NMR Analysis & Consulting of Decatur, IL.


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Copyright information

© Springer Science+Business Media, LLC 2009

Authors and Affiliations

  • George D. Bennett
    • 1
  • Lauren R. Bringman
    • 1
  • Elise M. Wildman
    • 1
  • Kraig A. Wheeler
    • 2
  1. 1.Department of ChemistryMillikin UniversityDecaturUSA
  2. 2.Department of ChemistryEastern Illinois UniversityCharlestonUSA

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