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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 16
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Original Articles

Intramolecular Cyclization of 1-(ω-Phenylalkyl)-2-(nitromethylene)pyrrolidines in Triflic Acid

Bamba Fanté Laboratoire de Chimie Organique Structurale, Université Félix Houphouët-Boigny, Abidjan, Côte d'IvoireCorrespondence[email protected]
,
Yaya Soro Laboratoire des Procédés Industriels de Synthèse, de l'Environnement et des Énergies Nouvelles, Institut National Polytechnique Félix Houphouët-Boigny, Yamoussoukro, Côte d'Ivoire
,
Sorho Siaka Laboratoire des Procédés Industriels de Synthèse, de l'Environnement et des Énergies Nouvelles, Institut National Polytechnique Félix Houphouët-Boigny, Yamoussoukro, Côte d'Ivoire
,
Jérôme Marrot Laboratoire ILV-UVSQ-UMR 8180 CNRS, Versailles, France
&
Jean-Marie Coustard Laboratoire IC2MP-UMR 7285 CNRS, Poitiers, France
Pages 2377-2385 | Received 06 Nov 2013, Published online: 13 Jun 2014
 
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Abstract

1-(ω-Phenylalkyl)-2-(nitromethylene)pyrrolidines in triflic acid undergo a C,O-diprotonation, followed by loss of water, to form conjugated iminium–hydroxynitrilium dications, which react with the tethered phenyl ring by electrophilic aromatic substitution to afford tricyclic iminium compounds as triflate salts. The scope and mechanism of this reaction are discussed.

GRAPHICAL ABSTRACT

Notes

Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.

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