Gas-phase pyrolysis of benzo- and naphthofuran derivatives

[Display omitted] •FVP of aminobenzo- and naphthofurans give formylbenzo- and naphthonitriles.•Absence of amino group renders cleavage of furan ring more difficult.•Substituted phenoxy and naphthoxy carbenes isomerize to benzaldehyde and naphthocarboaldehyde derivatives. Benzo- and naphthofuran carb...

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Bibliographic Details
Published in:Journal of analytical and applied pyrolysis 2019-09, Vol.142, p.104626, Article 104626
Main Authors: Ibrahim, Yehia A., Mohamed, Asaad S., Habib, Osama M., Al-Awadhi, Fatma H., Al-Jalal, Nader A., Al-Awadi, Nouria A.
Format: Article
Language:English
Subjects:
2-formylbenzonitrile
2-formylnaphthonitrile
Benzo- and naphthofuran derivatives
Gas-phase pyrolysis
Reaction mechanism
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Summary:[Display omitted] •FVP of aminobenzo- and naphthofurans give formylbenzo- and naphthonitriles.•Absence of amino group renders cleavage of furan ring more difficult.•Substituted phenoxy and naphthoxy carbenes isomerize to benzaldehyde and naphthocarboaldehyde derivatives. Benzo- and naphthofuran carboxylates 1, 2 and carboxamides 3, 4 were synthesized and pyrolysed by flash vacuum pyrolysis at 550 and 650 °C/10−2 mmHg. 2-Formylbenzonitrile 7 from benzofurans and 2-formylnaphthonitrile 14 from naphthofurans were isolated and identified as major products. The mechanism suggested for these pyrolytic reactions involves elimination of alcohol and amine from carboxylates 1, 2 and carboxamides 3, 4 respectively, followed by extrusion of CO to form phenoxy and naphthoxycarbenes that leads to 7 and 14 respectively.
ISSN:0165-2370
1873-250X
DOI:10.1016/j.jaap.2019.05.015