Intramolecular transformations of 3-cyanoamino- and 3-cyanoimino-1,2-diferrocenylcyclopropenes.
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, (1)H- and (13)C-NMR spectroscopy and mass spectrometry. The structures of compounds 7a and 10 were additionally confirmed by their X-ray diffraction analysis data.
Universidad Nacional Autónoma de México, Facultad de Química, Cd. Universitaria, Coyoacán,C.P. 04510, México D.F., Mexico. eiklimova@yahoo.com.mx
Elena Ivanovna
EI
Klimova
Tatiana
T
Klimova
Marcos
M
Flores-Alamo
Leon Vladimirovich
LV
Backinowsky
Marcos Martinez
MM
Garcia
D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*
D003517:Cyclopentanes; D006834:Hydrazines; D007202:Indicators and Reagents; D009570:Nitriles