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DOI: 10.1055/s-2005-861807
One-Pot Synthesis of Spirofuran and Benzocycloalka[1,2-b]furan Derivatives Using Manganese(III)-Mediated Oxidative Radical Cyclization
Publication History
Publication Date:
09 February 2005 (online)
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Abstract
New spiro[furan-2(3H),1′-(benzocycloalkane)] derivatives were obtained by the oxidation of methylenebenzocycloalkanes with manganese(III) acetate in the presence of 1,3-dicarbonyl compounds. A similar oxidation of the benzocycloalkene derivatives produced the functionalized benzocycloalka[1,2-b]furans in good yields. However, 1-benzyl-3,4-dihydronaphthalene gave both the corresponding spirofuran and benzocyclohexa[1,2-b]furan under the same oxidation conditions. The acid-catalyzed ring-opening reaction of the spirofurans and benzocycloalka[1,2-b]furans was also investigated.
Key words
oxidations - radicals - cyclizations - spiro compounds - furans - manganese
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PM3 calculation was performed by CAChe version 4.9.3.
15Crystal Structure Analysis Package, Molecular Structure Corporation: 1985 and 1992.