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Synthesis 2010(12): 2049-2056  
DOI: 10.1055/s-0029-1218773
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Fulvadienes Derived from Fluorenes and Their Oxidation to Spirodiaza­tetracenes

Gunther Buehrdela, Rainer Beckert*a, Helmar Görlsb
a Institute of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany
Fax: +49(3641)948212; e-Mail: C6bera@uni-jena.de;
b Institute of Inorganic and Analytical Chemistry, Friedrich-Schiller-University Jena, Lessingstr. 8, 07743 Jena, Germany
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Publication History

Received 5 February 2010
Publication Date:
05 May 2010 (online)

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Abstract

Based on the acylation reaction of fluorenyl anions with the bis(imidoyl) chlorides of oxalic acid, a short and efficient synthesis for a series of novel bis(arylamino) fulvadienes was developed. The products were isolated as red colored and crystalline compounds in good yields. Their structures were determined by elemental­ analysis, MS, NMR, and additionally by X-ray crystal structural analysis. Monoimidoyl chlorides showed the same reactivity. Enamines were isolated in good yields as products. The bis(arylamino) fulvadienes can be transformed by an oxidation-ring annulation sequence into diazatetracene derivatives. These to date unknown bis-spiro derivatives of diazatetracene are well soluble in common solvents and display green fluorescence in solution.

Key words

amines - oxidation - radical reaction - fulvadienes - bis(imidoyl) chlorides

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(10)CCDC-762471 (3a), CCDC-762472 (3d), CCDC-762473 (6b), and CCDC-762474 (7) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033; or deposit@ccdc.cam.ac.uk].