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Molecules 2009, 14(9), 3161-3175; https://doi.org/10.3390/molecules14093161

Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes

1
Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Coyoacán,C.P. 04510, México D.F., Mexico
2
N.D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russia
3
Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, C.P.04510, México D.F., Mexico
*
Author to whom correspondence should be addressed.
Received: 13 June 2009 / Revised: 20 July 2009 / Accepted: 12 August 2009 / Published: 26 August 2009
(This article belongs to the Special Issue Ferrocenes)
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Abstract

3-Cyanoamino-1,2- and -2,3-diferrocenylcyclopropenes 6a,b and 11a,b prepared by the reaction of diferrocenylcyclopropenylium salts with sodium cyanamide undergo smooth intramolecular transformations with both conservation of the three-membered ring [affording 3-cyanoimino-1,2-diferrocenylcyclopropene (8)] and its opening [affording Z-3-morpholino- and Z-3-piperidino-3-(cyanoimino)-1,2-diferrocenylprop-1-enes 7a,b and Z-3-cyanoimino-2,3-diferrocenyl-1-methylthioprop-1-ene (10)]. 3-Cyano-imino-1,2-diferrocenylcyclopropene (8) reacts with hydrazine to form 3-amino-6-ferrocenyl-5-ferrocenylmethyl-1,2,4-triazine (12) and Z-2,3-diferrocenylacrylohydrazide N-cyanoimide (13) as a result of intramolecular transformations. The structures of the compounds obtained were determined by IR, 1H- and 13C-NMR spectroscopy and mass spectrometry. The structures of compounds 7a and 10 were additionally confirmed by their X-ray diffraction analysis data.
Keywords: diferrocenylcyclopropenylium salts; cyanoamino(diferrocenyl)cyclopropenes; [amino(cyanoimino)methyl]-1; 2-diferrocenylethenes; 3-amino-6-ferrocenyl-5-ferrocenyl-methyl-1; 2; 4-triazine diferrocenylcyclopropenylium salts; cyanoamino(diferrocenyl)cyclopropenes; [amino(cyanoimino)methyl]-1; 2-diferrocenylethenes; 3-amino-6-ferrocenyl-5-ferrocenyl-methyl-1; 2; 4-triazine
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Klimova, E.I.; Klimova, T.; Flores-Alamo, M.; Backinowsky, L.V.; Garcia, M.M. Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes. Molecules 2009, 14, 3161-3175.

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