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Molecules 2011, 16(7), 5574-5590; doi:10.3390/molecules16075574

Intramolecular Conversions of (Aminoferrocenylpenta-1,4-dienyl)-ferrocenylcarbenes: Synthesis of Diferrocenylmono-, bi-, tricycles and Amino(diferrocenyl)hexa-1,3,5-trienes

1
Facultad de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, México D.F. 04510, Mexico
2
Centro de Investigación y Desarrollo Tecnológico en Electroquímica S.C. Parque Tecnológico Querétaro, Pedro de Escobedo, Querétaro 76703, Mexico
3
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow 119991, Russia
4
Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Coyoacán, México D.F. 04510, Mexico
*
Author to whom correspondence should be addressed.
Received: 23 May 2011 / Revised: 18 June 2011 / Accepted: 28 June 2011 / Published: 30 June 2011
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Abstract

Synthesis of 3,4-diferrocenyltoluene (7), 1-morpholino- and 1-piperidino-2,3-diferrocenylbicyclo[3.1.0]hex-2-enes 8a, 8b, 1-morpholino- and 1-piperidino-7-ferrocenyl-3,4-ferrocenobicyclo[3.2.1]oct-6-enes 9a, 9b, 2- and 3-amino(diferrocenyl)-hexa-1,3,5-trienes 10a,b, 11a,b by reactions of amino(diferrocenyl)cyclopropenylium tetrafluoro-borates with 1-methylprop-2-enylmagnesium chloride at 80 °C is described. The structures of the compounds obtained were determined by IR, 1H- and 13C-NMR spectroscopy and mass spectrometry. X-ray diffraction data for 1-piperidino-7-ferrocenyl-3,4-ferroceno-bicyclo[3.2.1]oct-6-ene (9b), 2-morpholino- and 2-piperidino-1,3-diferrocenyl-4-methyl-hexa-1,3,5-trienes 10a and 10b is presented. The electrochemical behaviour of compounds 7, 8a, 10a and 10b was investigated by means of cyclic voltammetry and square wave voltammetry. For 7 and 8a two electrochemical processes (I-II), attributed to the oxidation of the ferrocene moieties were found. On the other hand for compounds 10a and 10b a single electron transfer for both ferrocene groups and the electrochemical generation of the monocation and dication species were detected.
Keywords: amino(diferrocenyl)cyclopropenylium; cyclopropene ring opening; intramolecular conversion of aminoferrocenylpenta-1,4-dienyl(ferrocenyl)carbenes; 3,4-diferrocenyltoluene; amino(diferrocenyl)bicyclo-[3.1.0]hexanes; amino(ferrocenyl)-ferrocenobicyclo[3.2.1]octenes; amino(diferrocenyl)hexa-1,3,5-trienes; electrochemistry amino(diferrocenyl)cyclopropenylium; cyclopropene ring opening; intramolecular conversion of aminoferrocenylpenta-1,4-dienyl(ferrocenyl)carbenes; 3,4-diferrocenyltoluene; amino(diferrocenyl)bicyclo-[3.1.0]hexanes; amino(ferrocenyl)-ferrocenobicyclo[3.2.1]octenes; amino(diferrocenyl)hexa-1,3,5-trienes; electrochemistry
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Klimova, E.I.; Ortiz-Frade, L.A.; González-Fuentes, M.A.; Flores-Alamo, M.; Backinowsky, L.V.; García, M.M. Intramolecular Conversions of (Aminoferrocenylpenta-1,4-dienyl)-ferrocenylcarbenes: Synthesis of Diferrocenylmono-, bi-, tricycles and Amino(diferrocenyl)hexa-1,3,5-trienes. Molecules 2011, 16, 5574-5590.

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