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

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

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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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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