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

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

1,* , 2, 2, 1, 3 and 4
Received: 23 May 2011; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

Klimova EI, Ortiz-Frade LA, González-Fuentes MA, Flores-Alamo M, Backinowsky LV, García MM. Intramolecular Conversions of (Aminoferrocenylpenta-1,4-dienyl)-ferrocenylcarbenes: Synthesis of Diferrocenylmono-, bi-, tricycles and Amino(diferrocenyl)hexa-1,3,5-trienes. Molecules. 2011; 16(7):5574-5590.

Chicago/Turabian Style

Klimova, Elena I.; Ortiz-Frade, Luis A.; González-Fuentes, Miguel A.; Flores-Alamo, Marcos; Backinowsky, Leon V.; García, Marcos Martínez. 2011. "Intramolecular Conversions of (Aminoferrocenylpenta-1,4-dienyl)-ferrocenylcarbenes: Synthesis of Diferrocenylmono-, bi-, tricycles and Amino(diferrocenyl)hexa-1,3,5-trienes." Molecules 16, no. 7: 5574-5590.


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