Dicyanomethylene Compounds as Cyanation Reagents [1]*
Dietrich Döpp
a, Sabine Jüschke
a, and Gerald Henkel
ba 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.
