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Issue 13, 2010
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Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions

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Abstract

Flash vacuum pyrolysis (FVP) of aryl 2-(allyloxy)benzoates 5 and of the corresponding aryl 2-(allylthio)benzoates 6 at 650 °C, gives dibenzofurans 19 and dibenzothiophenes 20, respectively. The mechanism involves generation of phenoxyl (or thiophenoxyl) radicals by homolysis of the O-allyl (or S-allyl) bond, followed by ipso attack at the ester group, loss of CO2 and cyclisation of the resulting aryl radical. Synthetically, the procedure works well for p-substituted substrates, which lead to 2-substituted dibenzofurans 19b–f (73–90%) and dibenzothiophenes 20b–c (90–94%). Little selectivity is shown in the cyclisation of m-substituted substrates and competing interactions of the radical with the substituent—and ipso-attack—complicate the pyrolyses of o-substituted substrates. FVP of related radical precursors including 2-(allyloxy)phenyl benzoates 43 gave no dibenzofurans, whereas 2-(allyloxy-5-methyl)azobenzene 44 gave a much reduced yield. No carbazoles were obtained by FVP of 4-methylphenyl 2-(allylamino)benzoate 42.

Graphical abstract: Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions

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Supplementary files

Article information


Submitted
10 Feb 2010
Accepted
06 Apr 2010
First published
11 May 2010

Org. Biomol. Chem., 2010,8, 2961-2967
Article type
Paper

Formation of dibenzofurans by flash vacuum pyrolysis of aryl 2-(allyloxy)benzoates and related reactions

M. Black, J. I. G. Cadogan and H. McNab, Org. Biomol. Chem., 2010, 8, 2961
DOI: 10.1039/C002480E

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