Concise, aromatization-based approach to an elaborate C2-symmetric pyrenophane

Penchal Reddy Nandaluru; Prateek Dongare; Christina M. Kraml; Robert A. Pascal; Louise N. Dawe; David W. Thompson; Graham J. Bodwell

doi:10.1039/C2CC33611A

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Concise, aromatization-based approach to an elaborate C₂-symmetric pyrenophane†‡

Penchal Reddy Nandaluru,^a Prateek Dongare,^a Christina M. Kraml,^b Robert A. Pascal, Jr.,^c Louise N. Dawe,^a David W. Thompson^a and Graham J. Bodwell*^a

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* Corresponding authors

^a Department of Chemistry, Memorial University, St. John’s, NL, Canada
E-mail: gbodwell@mun.ca
Fax: +1 709 864 3702
Tel: +1 709 864 8406

^b Lotus Separations LLC, Department of Chemistry, Princeton University, Princeton, USA

^c Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, USA

Abstract

A very short synthesis (5 steps), the crystal structure and resolution of an elaborate, inherently chiral [n](1,6)pyrenophane is reported. The synthesis hinges upon two very productive events: a multicomponent reaction and an unprecedented double-McMurry/valence isomerization/dehydrogenation step. Aromatization reactions are involved in the formation of all four of the rings of the pyrene system.

This article is part of the themed collection: Aromaticity

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Article information

DOI: https://doi.org/10.1039/C2CC33611A
Article type: Communication
Submitted: 18 May 2012
Accepted: 12 Jun 2012
First published: 14 Jun 2012

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Chem. Commun., 2012,48, 7747-7749

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Concise, aromatization-based approach to an elaborate C₂-symmetric pyrenophane

P. R. Nandaluru, P. Dongare, C. M. Kraml, R. A. Pascal, L. N. Dawe, D. W. Thompson and G. J. Bodwell, Chem. Commun., 2012, 48, 7747 DOI: 10.1039/C2CC33611A

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