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Synlett 1994; 1994(6): 459-460
DOI: 10.1055/s-1994-22890
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Generation and [4+2] Cycloadditions of Dimethyl-4,5-bis(bromomethylene)furan-2,3-dioate, a Furan Analogue of o-Quinodimethane

Mouaffak Al Hariri* , Félix Pautet, Houda Fillion
  • *Laboratoire de Chimie Organique, Institut des Sciences Pharmaceutiques et Biologiques, Université Claude Bernard, 8 Avenue Rockefeller, 69373 Lyon, France
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Publication Date:
18 September 2002 (online)

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Dimethyl-4,5-bis(bromomethylene)furan-2,3-dioate, a furan analogue of o-quinodimethane, is generated "in situ" from the 4,5-bis(dibromomethyl) derivative through a sodium iodide-induced 1,4-elimination process. Trapping of the unstable intermediate with maleimides or quinones affords the aromatised Diels-Alder cycloadducts.

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