1,3-Dipolar cycloaddition of several azomethine ylides to [60]fullerene: synthesis of derivatives of 2′,5′-dihydro-1′H-pyrrolo[3′,4′ : 1,2][60]fullerene 1

Wu, Shuisheng; Sun, Wei-Quan; Zhang, Dan‐Wei; Shu, Le; Wu, Hou‐Ming; Xu, Jing-Fei; Lao, Xia-Fei

doi:10.1039/a705962k

Cited by 35 publications

(10 citation statements)

References 20 publications

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“…The purity and the identity of compounds were assessed and confirmed by standard spectroscopic methods. The structure of compounds 3 and 6 was elucidated by the comparison of the obtained spectroscopic data with those reported in the literature . Because no differences either in the spectrometric behavior or under heating conditions between cis ‐ and trans ‐isomers were found, we used for all our investigations the corresponding cis ‐isomers of compounds 1–10 .…”

Section: Methodsmentioning

confidence: 99%

Effect of substituents and protonation on the mechanism of 1,3‐dipolar retro‐cycloaddition reaction of pyrrolidino[60]‐ and [70]fullerenes

et al. 2011

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The mass spectra of new substituted pyrrolidino[60]- and [70]fullerenes have been obtained using electrospray ionization conditions in the positive and negative mode of detection with two different mass spectrometers, a quadrupole ion trap and a Fourier transform ion cyclotron resonance. Radical anions M(●-) and deprotonated molecules [M-H](-) are formed under negative electrospray ionization mass spectrometry conditions, and the collision-induced dissociations of both ionic species have been studied. Either negative odd-electron ions or negative even-electron ions undergo a retro-cycloaddition process forming the corresponding fullerene product ions C(60)(●-) and C(70)(●-). The generation of fullerene radical anions from deprotonated molecules is a new exception of the "even-electron rule." In contrast, the protonated molecules [M + H](+) obtained from the positive mode of detection do not undergo this cycloreversion reaction, and the MS(n) experiment reveals a variety of eliminations of neutral molecules involving different hydrogen shifts and multiple bond cleavages that lead eventually to substituted methanofullerene fragment ions. The observed fragmentations can be correlated with the electronic character of the substituents attached to the heterocyclic moiety. The results obtained from the thermal reactions of these compounds, carried out under different pH conditions, correlate well with those obtained in gas phase. The different behaviors between protonated and unprotonated molecules and ions can be explained assuming that the retro-cycloaddition reaction takes place only when the nitrogen atom of the pyrrolidine ring (the basic center of the molecule) is unprotonated both in gas and condensed phase. The protonation of the NH group inhibits the cycloreversion process, and therefore different fragmentations take place. The detailed mechanisms of the formation and evolution of the intermediate fragments are described.

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Section: Methodsmentioning

confidence: 99%

Effect of substituents and protonation on the mechanism of 1,3‐dipolar retro‐cycloaddition reaction of pyrrolidino[60]‐ and [70]fullerenes

et al. 2011

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“…It is worth noting that by the beginning of our studies several examples of thermal and Li-promoted reactions of 1,3,5-perhydrotriazines synthesized from glycine esters and formaldehyde with fullerene C 60 were reported in the literature (Scheme ). When an activated methylene group is present in the initial perhydrotriazine, 2-substituted pyrrolidino[3′,4′:1,9]fullerene molecules are formed under the reaction conditions.…”

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confidence: 99%

One-Pot Method for the Synthesis of 2,5-Unsubstituted Pyrrolidino[3′,4′:1,9]fullerenes

2017

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“…6,7 Such highly reactive intermediates are usually produced in situ, by the condensation of α-amino acids with carbonyl compounds and further decarboxylation of obtained iminium salts. 6,7 Furthermore, other approaches for azomethine ylides preparation have been designed, including acid-catalyzed, 8 photochemical 9 or thermal 10 desilylation of trimethylsilyl amino derivatives, tautomerization of imines, 11,12 as well as photochemically-induced reactions of tertiary amines. 13,14 At the same time, variously substituted fulleropyrrolidines have also been prepared utilizing many other methods, such as thermal reactions of aromatic aldehydes and various primary amines, 15,16 thermal and photochemical reactions of α-amino acids and amino acid esters without an aldehyde, 17,18 reaction of amino acids and quaternary ammonium salts 19 or reaction of halides and α-amino acids 20 with C60.…”

Section: Introductionmentioning

confidence: 99%

Fulleropyrrolidines with orthogonally flexible substituents - synthesis and electrochemical properties

Jovanović

Stanojkovic

Halilovic

et al. 2021

JSCS

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A large series of disubstituted fulleropyrrolidines was synthesized and analyzed by the cyclic voltammetry. The three main groups of target compounds differ by a flexible N-chain, while their further diversity was achieved by the introduction of various rigid, aryl substituents at pyrrolidine carbon. Some dialkyl analogues were designed for comparison, as well. A standard [3+2]-cycloaddition of in situ generated azomethine ylides to C60 afforded a variety of disubstituted fulleropyrrolidines. Furthermore, a set of dumbbell-shaped di(fulleropyrrolidine) derivatives containing rigid fumaryl or isophthaloyl diamide platform was prepared in aim to investigate a long-range effect of the second fulleropyrrolidine moiety on electrochemical properties. All compounds were fully characterized by comparative analysis of spectral data, while examination of electrochemical properties was performed on representative samples, distinguished by main structural subunits. All compounds expressed quite similar electron-accepting ability, lower than C60, but higher in comparison to structurally similar N-methylfulleropyrrolidine.

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1,3-Dipolar cycloaddition of several azomethine ylides to [60]fullerene: synthesis of derivatives of 2′,5′-dihydro-1′H-pyrrolo[3′,4′ : 1,2][60]fullerene 1

Cited by 35 publications

References 20 publications

Effect of substituents and protonation on the mechanism of 1,3‐dipolar retro‐cycloaddition reaction of pyrrolidino[60]‐ and [70]fullerenes

Effect of substituents and protonation on the mechanism of 1,3‐dipolar retro‐cycloaddition reaction of pyrrolidino[60]‐ and [70]fullerenes

One-Pot Method for the Synthesis of 2,5-Unsubstituted Pyrrolidino[3′,4′:1,9]fullerenes

Fulleropyrrolidines with orthogonally flexible substituents - synthesis and electrochemical properties

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