ChemInform Abstract: Synthesis of Methano[60]fullerenephosphonic‐ and Methano[60]fullerene‐diphosphonic Acids.

Pellicciari, Roberto; Natalini, Benedetto; Amori, Laura; Marinozzi, Maura; Seraglia, Roberta

doi:10.1002/chin.200110105

Cited by 7 publications

(8 citation statements)

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“…For example, a solution of [60]fullerene in toluene was treated with the diazoamide 53 at reux for 48 h providing the fullerenyl amino ester 52 (R ¼ Bn) in 30% yield (Scheme 9). 14 Thermal reactions of [60]fullerene with other diazo compounds such as diazomethanes, 15 diazoacetates, 16 diazoamides, diazomethylphosphonates, 17 and diazoketones, provides a broad variety of methano[60]fullerenes, having handles for further functionalization. The methano[60] fullerene 51 can be accessed from either the tert-butyl ester 54 (Scheme 10) or the O-glycolic ester 49 (Scheme 9), followed by ester deprotection of the fullerenyl adducts 55 and 50, respectively.…”

Section: Assocmentioning

confidence: 99%

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

2014

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This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides. The applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted. This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides. Disciplines Medicine and Health Sciences | Social and Behavioral SciencesThe applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted.

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Section: Assocmentioning

confidence: 99%

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

2014

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“…Analogous reactions with disubstituted diazomethanes generated in situ from unsymmetrical ketone hydrazones were characterized by lower selectivity, and mixtures of stereoisomeric homofullerenes were obtained [12,13,15]. The proposed catalytic procedure is considerably more advantageous than known thermal cycloadditions of diazoalkanes to fullerene C 60 [17][18][19][20][21]. Reactions of carbon clusters with diazo compounds were reviewed in detail in [2].…”

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confidence: 98%

Catalytic cycloaddition of diazoalkanes with heterocyclic substituents to fullerene C60

et al. 2012

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Methanofullerenes were directly synthesized under mild conditions by cycloaddition to fullerene C 60 of diazoalkanes generated in situ by oxidation of ketone hydrazones containing a heterocyclic fragment with manganese(IV) oxide in the presence of the catalytic system Pd(acac) 2 -2 PPh 3 -4 Et 3 Al.Methanofullerenes available via Bingel-Hirsch reaction constitute now one of the most promising classes of fullerenes from the view point of practical applications. Methanofullerenes can be used in the manufacture of highly efficient solar batteries and in the preparation of drugs for the treatment of most dangerous human diseases [1,2]. Apart from the BingelHirsch reaction, methods based on cycloaddition of diazo compounds to carbon clusters have found wide application in synthetic practice; however, these procedures generally lead to the formation of mixtures of stereoisomeric homo-and methanofullerenes. The use of metal complex catalysts makes it possible to direct the cycloaddition of diazo compounds to fullerenes toward formation of individual methanofullerenes. Complexes based on palladium and rhodium were reported to successfully catalyze reactions of fullerene C 60 with diazomethanes [3], diazoacetates [4][5][6][7], and diazo ketones [8-10], and the corresponding cyclopropafullerenes were obtained with high selectivity.We recently showed that homofullerenes and spiro homofullerenes can be synthesized with high selectivity by reaction of C 60 with monosubstituted diazomethanes and cyclic diazoalkanes generated in situ by oxidation of the corresponding hydrazones in the presence of Pd(acac) 2 -PPh 3 -Et 3 Al as catalytic system [11][12][13][14][15][16]. We thus obtained pure [5,6]-open cycloadducts in which bulkier substituent was located above the five-membered fragment of C 60 . Analogous reactions with disubstituted diazomethanes generated in situ from unsymmetrical ketone hydrazones were characterized by lower selectivity, and mixtures of stereoisomeric homofullerenes were obtained [12, 13,15]. The proposed catalytic procedure is considerably more advantageous than known thermal cycloadditions of diazoalkanes to fullerene C 60 [17][18][19][20][21]. Reactions of carbon clusters with diazo compounds were reviewed in detail in [2].In continuation of our studies on cycloaddition of diazo compounds to fullerenes, in the present work we Me O I Scheme 1.

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“…The compositions of fullereno pyrrolidines 5-8 were confirmed by MALDI TOF mass spectrometry. The mass spectra contain molecular ion peaks at m/z 1067.75 (calculated 1067.99) (5), m/z 1129.98 (calculated 1130.07) (6), m/z 1019.44 (calculated 1020.03) (7), and m/z 1021.71 (calculated 1021.99) (8). The UV spectra of compounds 5-8 show characteristic ab sorption bands at 258, 268, 328, and 430 nm, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structures, and properties of new thiophosphorylated fullerenopyrrolidines. First example of the Pishchimuka reaction in fullerene derivatives

et al. 2006

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The reactions of fullerene C 60 with thiophosphorylated mono or dialdehydes and N methylglycine in toluene afforded new thiophosphorylated fullerenopyrrolidines, including those containing the free aldehyde group. The purity and compositions of the reaction products were confirmed by MALDI TOF mass spectrometry and HPLC. The structures of the reaction products were established by two dimensional homo and heterocorrelation NMR experi ments. The properties of the products were studied by cyclic voltammetry and quantum chemi cal methods. The Pishchimuka rearrangement in thiophosphorylated derivatives of fullereno pyrrolidines was performed for the first time, and thiol esters of phosphonic acids of fullerenopyrrolidines were prepared.

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ChemInform Abstract: Synthesis of Methano[60]fullerenephosphonic‐ and Methano[60]fullerene‐diphosphonic Acids.

Cited by 7 publications

References 1 publication

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

Catalytic cycloaddition of diazoalkanes with heterocyclic substituents to fullerene C60

Synthesis, structures, and properties of new thiophosphorylated fullerenopyrrolidines. First example of the Pishchimuka reaction in fullerene derivatives

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