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Dicyanomethylene Compounds as Cyanation Reagents [1]* Dietrich Döpp

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Dicyanomethylene Compounds as Cyanation Reagents [1]*

Dietrich Döpp

a

, Sabine Jüschke

a

, and Gerald Henkel

b

a Fachgebiet Organische Chemie und

b Fachgebiet Festkörperchemie, Institut für Chemie, Gerhard-Mercator-Universität Duisburg, D-47048 Duisburg, Germany

Reprint requests to Prof. Dr. D. Döpp, Fax +49(0)2 03-3 79 41 92.

E-mail: doepp@uni-duisburg.de

Dedicated to Professor W. S. Veeman on the occasion of his 60th birthday Z. Naturforsch.57 b, 460Ð470 (2002); received February 1, 2002

Dihydroisoquinolines, Bridged Functional Biphenyls, Cyclic Iminium Ions

Ethenetetracarbonitrile (2, in benzene solution) and 1,3-dioxoindan-2-ylidene propanedini- trile (4, in ethanol or acetonitrile solution) act onN-aryl-2,3-dihydro-1H-benz[d,e]isoquino- lines6a-dand N-aryl-6,7-dihydro-5H-dibenz[c,e]azepines11a-dviahydride abstraction fol- lowed by addition of cyanide to the iminium carbon atom forming the corresponding 1- and 5-carbonitriles9a-dand13a-d, respectively, in moderate to medium yields. Additionally, the known 1,3-dihydroxy-2H-inden-2-ylidenepropanedinitrile 15 and a novel dispirocyclopro- pane (17) are formed from4in the reaction with6in acetonitrile and ethanol, respectively.

The structures of 17 and 6-(4-methylphenyl)-6,7-dihydro-5H-dibenz[c,e]azepine-5-carbonit- rile have been unambiguously confirmed by single-crystal X-ray crystallography.

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