Superacid-promoted synthesis of polychlorinated dibenzofurans

Superacid-promoted synthesis of polychlorinated dibenzofurans

[Display omitted] •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. Polychlorinated dibenzofurans...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 57; no. 33; pp. 3711 - 3714
Main Authors: Qarah, Ahmad, Gasonoo, Makafui, Do, Dat, Klumpp, Douglas A.
Format: Journal Article
Language:English
Published: Elsevier Ltd 17-08-2016
Subjects:
Condensation
Dibenzofurans
Dioxins
Heterocycles
Superacid
Superacid
Dioxins
Heterocycles
Dibenzofurans
Condensation
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Summary:[Display omitted] •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. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.06.100