Issue 60, 2013
From the journal:

Chemical Communications

Oxidative electrochemical aryl C–C coupling of spiropyrans†

Oleksii Ivashenko,‡a   Jochem T. van Herpt,‡b   Petra Rudolf,a   Ben L. Feringaab  and  Wesley R. Browne*ab  

* Corresponding authors

a Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
E-mail: w.r.browne@rug.nl
Tel: +31 50 363 4428

b Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands

Abstract

The isolation and definitive assignment of the species formed upon electrochemical oxidation of nitro-spiropyran (SP) is reported. The oxidative aryl C–C coupling at the indoline moiety of the SP radical cation to form covalent dimers of the ring-closed SP form is demonstrated. The coupling is blocked with a methyl substituent para to the indoline nitrogen.

Graphical abstract: Oxidative electrochemical aryl C–C coupling of spiropyrans

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Article information

DOI
https://doi.org/10.1039/C3CC42396D
Article type
Communication
Submitted
02 Apr 2013
Accepted
11 Jun 2013
First published
11 Jun 2013

Chem. Commun., 2013,49, 6737-6739

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Oxidative electrochemical aryl C–C coupling of spiropyrans

O. Ivashenko, J. T. van Herpt, P. Rudolf, B. L. Feringa and W. R. Browne, Chem. Commun., 2013, 49, 6737 DOI: 10.1039/C3CC42396D

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