Superacid-promoted synthesis of polychlorinated dibenzofurans. Issue 33 (17th August 2016)

• Record Type: Journal Article
• Authors: Qarah, Ahmad; Gasonoo, Makafui; Do, Dat; Klumpp, Douglas A.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 33(2016)
• Page Start: 3711
• Page End: 3714
• Publication Date: 2016-08-17
• Subjects: Heterocycles -- Superacid -- Condensation -- Dioxins -- Dibenzofurans; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.100
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A one step procedure has been developed for the synthesis of polychlorinated dibenzofurans. The chemistry involves a superacid-promoted condensation reaction of o -chloranil and arenes. An unusual carbocation cyclization is proposed for the conversion. Abstract: Polychlorinated dibenzofurans have been prepared in one step by the condensations of o -chloranil with arenes in triflic acid. A mechanism is proposed involving formation of a monoprotonated quinone (carboxonium ion), electrophilic attack at the arene, and cyclization of a carbocation intermediate. The chemistry is further examined by spectroscopic and theoretical studies.