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Synthesis 1990; 1990(7): 583-584
DOI: 10.1055/s-1990-26947
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2,3-Dihydro-1,4-dioxin in Organic Chemistry. Part X.1 A new Synthesis of 3-Hydroxy-3-cyclobutene-1,2-dione (Semisquaric acid)

Marcel Fétizon* , Issam Hanna
  • *Laboratoire de Synthèse Organique, Ecole Polytechnique, F-91128 Palaiseau Cedex, France
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Publikationsdatum:
17. September 2002 (online)

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Cycloaddition of 2,3-dihydro-1,4-dioxin (1) to 1,1-dichloroketene, generated from zinc and trichloroacetyl chloride by sonication, leads to 7,7-dichloro-2,5-dioxabicyclo[4.2.0]octan-8-one (2) which upon acid hydrolysis affords semisquaric acid (3-hydroxy-3-cyclobutene-1,2-dione, 3).