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Synthesis 1989; 1989(12): 942-944
DOI: 10.1055/s-1989-27438
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Alkyl Isobenzofurans from Phthalides; Inter and Intramolecular Diels-Alder Reactions

Sanath K. Meegalla* , Russell Rodrigo
  • *Guelph-Waterloo Centre for Graduate Work in Chemistry, Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1
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Publication Date:
02 May 2002 (online)

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A general procedure for the conversion of phthalides 1 to alkyl isobenzofurans 4 is described and illustrated with nine. examples. Thus, the alkylidene phthalans 3 produced from the phthalides 1 in one step are in acid catalyzed equilibrium with the. alkyl isobenzofurans 4 which are trapped in situ by dienophiles as the inter- and intramolecular Diels-Alder adducts 5-9.