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Synlett 1996; 1996(12): 1143-1147
DOI: 10.1055/s-1996-5699
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Recent Developments in the Cycloaddition Reactions of o-Benzoquinones

Vijay Nair* , Sasi Kumar
  • *Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum-695 019, India, E-mail: rrlt@sirnetm.ernet.in, Fax: 91-471-490186
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Publication Date:
31 December 2000 (online)

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o-Benzoquinones display multiple reaction profiles in cycloaddition reactions. With electron rich dienes, benzodioxin structures resulting from a [3,3] sigmatropic rearrangement of the initially formed spirocyclic compounds are obtained. 6-Aryl and 6,6-dialkyl fulvenes give rise to bicyclo[2.2.2] adducts, whereas 6,6-tetramethylenefulvene undergoes rearrangement to cyclopent-1-enyl cyclopentadiene prior to cycloaddition to the dicarbonyl system leading to benzodioxins. The bicyclo[2.2.2]octene diones derived from o-benzoquinones undergo a number of synthetically useful transformations.

o-Benzoquinone - Cycloaddition - Benzodioxin - Bicyclo[2.2.2]octene dione - Pyrrolenobenzodioxin