A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction

Christopher L. Anderson; Jiatao Liang; Simon J. Teat; Andrés Garzón-Ruiz; David P. Nenon; Amparo Navarro; Yi Liu

doi:10.1039/D0CC00916D

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A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction†

Christopher L. Anderson,

^ab Jiatao Liang,

^ab Simon J. Teat,

^c Andrés Garzón-Ruiz,

^d David P. Nenon,

^be Amparo Navarro

^f and Yi Liu

*^a

Author affiliations

* Corresponding authors

^a The Molecular Foundry, Lawrence Berkeley National Laboratory, One Cyclotron Road, Berkeley, California 94720, USA
E-mail: yliu@lbl.gov

^b Department of Chemistry, University of California, Berkeley, California 94720, USA

^c Advanced Light Source, Lawrence Berkeley National Laboratory, One Cyclotron Road, Berkeley, California 94720, USA

^d Department of Physical Chemistry, Faculty of Pharmacy, Universidad de Castilla-La Mancha, Cronista Francisco Ballesteros Gómez, 02071 Albacete, Spain

^e Materials Sciences Division, Lawrence Berkeley National Laboratory, One Cyclotron Road, Berkeley, California 94720, USA

^f Department of Physical and Analytical Chemistry, Faculty of Experimental Sciences, Universidad de Jaén, Paraje las Lagunillas, 23071 Jaén, Spain

Abstract

The generation of a highly-substituted [2.2](2,5)pyrazinophane via a cascade reaction is presented. The pyrazinophane product is formed via the dimerization of a member of the para-azaquinodimethane (p-AQM) family of conjugated quinoidal compounds—reactivity that sheds light on the nature of stability in p-AQMs. Additionally, the electronic and structural nature of this highly-strained ring system are characterized.

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DOI: https://doi.org/10.1039/D0CC00916D
Article type: Communication
Submitted: 04 Feb 2020
Accepted: 09 Mar 2020
First published: 10 Mar 2020

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Chem. Commun., 2020,56, 4472-4475

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A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction

C. L. Anderson, J. Liang, S. J. Teat, A. Garzón-Ruiz, D. P. Nenon, A. Navarro and Y. Liu, Chem. Commun., 2020, 56, 4472 DOI: 10.1039/D0CC00916D

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Chemical Communications

A highly substituted pyrazinophane generated from a quinoidal system via a cascade reaction†

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