Synthesis of stable 1-ethoxy-2,3-diferrocenylcyclopropenylium tetrafluoroborate and its reactions with lithium reagents

Klimova, Elena I.; Klimova, T. P.; Lara, Soledad Betanzos; Chavez, Jorge Dominguez; Ortega, Simón Hernández; Toscano, Rubén A.; García, Maribel Osorio

doi:10.1016/j.jorganchem.2005.08.038

Cited by 6 publications

(3 citation statements)

References 18 publications

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“…According to a standard procedure [ 5 , 6 , 7 ], 2,3-diferrocenylcyclopropenone [ 9 ] was first converted into 1-ethoxy-2,3-diferrocenylcyclopropenylium tetrafluoroborate and then to tetrafluoroborates 1a , b [ 1 , 2 ], which served as the starting materials in the present study.…”

Section: Resultsmentioning

confidence: 99%

“…The following reagents were purchased from Aldrich: Tetrachlorocycloropropene, 98%; ferrocene, 98%; triethyloxonium tetrafluoroborate, 1.0 M solution in dichloromethane; morpholine, 99.5%; piperidine, 99%; 1-methyl-2-propenylmagnesium chloride, 0.5M solution in tetrahydrofuran. Ethoxy-(diferrocenyl)cyclopropenylium tetrafluoroborate was obtained by treating 2,3-diferrocenylcyclo-propenone [ 2 ] in dichloromethane with triethyloxonium tetrafluoroborate. Diferrocenyl(morpholino)- or (piperidino)cyclopropenylium tetrafluoroborates 1a , b were obtained from ethoxy(diferrocenyl)-cyclopropenylium tetrafluoroborate and morpholine or piperidine in dichloromethane [ 1 ].…”

Section: Methodsmentioning

confidence: 99%

“…Diferrocenylcyclopropenylium cations with heterosubstituents in the small ring have recently been described [ 1 , 2 , 3 , 4 , 5 , 6 ]. These include 1-ethoxy-, 1-diethylamino-, 1-morpholino-, 1-piperidino-2,3-diferrocenylcyclopropenylium tetrafluoroborates and 2,3-diferrocenyl-1-methylsulfanylcyclo-propenylium iodide.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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

et al. 2011

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Reagent‐Controlled α‐Selective Dehydrative Glycosylation of 2,6‐Dideoxy‐ and 2,3,6‐Trideoxy Sugars

et al. 2016

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We have found that activating either 2,3-bis(2,3,4trimethoxyphenyl)cyclopropenone or 2,3-bis(2,3,4-trimethoxyphenyl)cyclopropene-1-thione with oxalyl bromide results in the formation of as pecies that promotes the glycosylation between 2,6-dideoxy-sugar hemiacetals and glycosyl acceptors in good yield and high a-selectivity.B oth reactions are mild and tolerate anumber of sensitive functional groups including highly acid-labile 2,3,6-trideoxy-sugar linkages.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.

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Reagent‐Controlled α‐Selective Dehydrative Glycosylation of 2,6‐Dideoxy‐ and 2,3,6‐Trideoxy Sugars

et al. 2016

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We have found that activating either 2,3-bis(2,3,4-trimethoxyphenyl)cyclopropenone or 2,3-bis(2,3,4-trimethoxyphenyl)cyclopropene-1-thione with oxalyl bromide results in the formation of a species that promotes the glycosylation between 2,6-dideoxy-sugar hemiacetals and glycosyl acceptors in good yield and high α-selectivity. Both reactions are mild and tolerate a number of sensitive functional groups including highly acid-labile 2,3,6-trideoxy-sugar linkages.

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Synthesis of stable 1-ethoxy-2,3-diferrocenylcyclopropenylium tetrafluoroborate and its reactions with lithium reagents

Cited by 6 publications

References 18 publications

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

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

Reagent‐Controlled α‐Selective Dehydrative Glycosylation of 2,6‐Dideoxy‐ and 2,3,6‐Trideoxy Sugars

Reagent‐Controlled α‐Selective Dehydrative Glycosylation of 2,6‐Dideoxy‐ and 2,3,6‐Trideoxy Sugars

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