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Synthesis 1999; 1999(4): 574-576
DOI: 10.1055/s-1999-3441
short paper
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A New Synthesis of cis-Cyclobut-3-ene-1,2-dicarboxylic Anhydride

Noëlle Gauvry* , Corinne Comoy, Cyrille Lescop, François Huet
  • *Laboratoire de Synthèse Organique, UPRES A CNRS 6011, Faculté des Sciences, Université du Maine, Avenue Olivier Messiaen, F-72085 Le Mans Cedex 9, France; Fax +33(2)43 83 33 66; E-mail: fhuet@aviion.univ-lemans.fr
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Publication History

Publication Date:
31 December 1999 (online)

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The title compound was prepared in two steps by [2 + 2] photochemical cycloaddition between (E)-1,2-dichloroethene and maleic anhydride followed by reductive chlorine elimination with activated zinc. This safe synthetic route gave cis-cyclobut-3-ene-1,2-dicarboxylic anhydride in good overall yield and could be carried out on a multigram scale.

cyclobutenes - photochemistry - [2 + 2] cycloaddition - reduction - activated zinc