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Synthesis 2001(12): 1812-1817
DOI: 10.1055/s-2001-17528
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Simple Access to Indolino-Azepines - A New Halochromic System for Information Recording

Yinmin Maa, Christian Webera, Thomas Hartmanna, Heinz Dürr*a, Carl Krügerb, J. Kossanyic
a FR 11.2, Organische Chemie, Universität des Saarlandes, 66041 Saarbrücken, Germany
Fax: +49(681)3024105; e-Mail: ch12hd@rz.uni-sb.de;
b Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany
c CNRS, 2-8 Rue Henri Dunant, 94320 Thiais, France
Further Information

Publication History

Received 14 March 2001
Publication Date:
11 August 2004 (online)

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Abstract

A new periselective reaction of an 8π-system is reported. This system is prepared by the reaction of spiro[2-cyclopropene-1,9Ž-fluorene]-2,3-dimethyldicarboxylates 2 with 2-styryl-3H-indoles 1 to afford azepine derivatives 4. The addition of acids to 4 causes an important color change, thus generating a new halochromic system.

Key words

electrocyclization - halochromism - heterocycles - cycloreversion

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Crystallographic data (excluding structure factors)for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre, Lensfield Road, Cambridge CB2 1EW, UK as supplementary publication under the number CCDC 117323.