Synthesis of Fullerooxazoles: Novel Reactions of [60]Fullerene with Nitriles Promoted by Ferric Perchlorate

Li, Fa‐Bao; Liu, Tongxin; Wang, Guan‐Wu

doi:10.1021/jo8007868

Cited by 96 publications

(46 citation statements)

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“…On the basis of the previously suggested mechanisms of the Fe(ClO 4 ) 3 -mediated reactions of C 60 with nitriles [54] and aldehydes/ketones [59], we proposed a possible mechanism for the reactions of C 60 with boronic acids promoted by Fe(ClO 4 ) 3 to afford fullerenyl boronic esters 29 (Scheme 16). Reaction of a chosen boronic acid with Fe(ClO 4 ) 3 could generate Fe(III)-complex 28 accompanied by the elimination of HClO 4 .…”

Section: Reactions Of C 60 With Arylboronic Acidsmentioning

confidence: 94%

“…In our previous work [54,59], we have disclosed the reactions of C 60 with nitriles and aldehydes/ketones promoted by Fe(ClO 4 ) 3 to afford the C 60 -fused oxazolines [54] and C 60 -fused 1,3-dioxolanes [59]. The reactions of C 60 with nitriles or aldehydes/ketones were believed to proceed via the Fe(ClO 4 ) 3 -mediated addition reaction of water to unsaturated carbon-nitrogen triple bond or unsaturated carbonoxygen double bond to produce the Fe(III)-complexes 19 and 24, respectively ( Figure 1).…”

Section: Reactions Of C 60 With Arylboronic Acidsmentioning

confidence: 96%

“…To our great satisfaction, the Fe(ClO 4 ) 3 -mediated reactions of C 60 with nitriles unexpectedly afforded the rare fullerooxazole derivatives 18 in 9%-22% yields (41%-84% based on consumed C 60 ) by the direct dissolution method (Scheme 8) [54]. The employed nitriles included 4-tolunitrile, benzonitrile, 4-methoxybenzonitrile, 3,4-dimethoxybenzonitrile, 4-bromobenzonitrile, 4-nitrobenzonitrile, phenylacetonitrile and ethyl cyanoacetate.…”

Section: Reactions Of C 60 With Nitrilesmentioning

confidence: 99%

“…In our previous study, we reported the synthesis of rare fullerooxazoles via the Fe(ClO 4 ) 3 -mediated reactions of C 60 with a variety of nitriles by the direct dissolution method [54]. should also proceed via a similar reacton pathway to afford the scarce C 60 -fused 1,3-dioxolane derivatives.…”

Section: Reactions Of C 60 With Aldehydes/ketonesmentioning

confidence: 99%

“…It is obvious that the mechanisms for the reactions of C 60 with methyl ketones promoted by Fe(ClO 4 ) 3 and Mn(OAc) 3 /Cu(OAc) 2 are completely different. On the basis of the previously reported formation pathway of fullerooxazoles [54] in the reactions of C 60 with various nitriles promoted by Fe(ClO 4 ) 3 , we proposed a possible mechanism for the Fe(ClO 4 ) 3 -mediated reactions of C 60 with aldehydes/ ketones to afford C 60 nation with another molecule of Fe(ClO 4 ) 3 to give Fe(III)-complex 26, followed by intramolecular cyclization accompanied with the loss of a Fe(II) species to afford C 60 -fused 1,3-dioxolanes 22/23. The C 60 -fused 1,3-dioxolane derivatives are valuable precursors and can be utilized for further functionalizations.…”

Section: Reactions Of C 60 With Aldehydes/ketonesmentioning

confidence: 99%

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Ferric perchlorate-mediated radical reactions of [60]fullerene

Wang

2012

Sci. China Chem.

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Transition-metal-salt-mediated radical reactions of fullerenes have attracted extensive attention as a new and important method for fullerene functionalization. The application of relatively cheap and easily available ferric perchlorate (Fe(ClO 4 ) 3 ) to the synthesis of [60]fullerene (C 60 ) has demonstrated remarkable advantages and afforded a series of novel fullerene derivatives. In this review we present our recent progress in this area and summarize the reactions of C 60 with malonate esters, β-keto esters, nitriles, aldehydes/ketones, and arylboronic acids in the presence of Fe(ClO 4 ) 3 to afford the C 60 -fused disubstituted lactones, C 60 -fused hemiketal, C 60 -fused dihydrofuran, C 60 -fused oxazoles, C 60 -fused 1,3-dioxolanes, and fullerenyl boronic esters. The possible reaction mechanisms for the above-mentioned reactions are also described in detail.

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Section: Reactions Of C 60 With Arylboronic Acidsmentioning

confidence: 94%

Section: Reactions Of C 60 With Arylboronic Acidsmentioning

confidence: 96%

Section: Reactions Of C 60 With Nitrilesmentioning

confidence: 99%

Section: Reactions Of C 60 With Aldehydes/ketonesmentioning

confidence: 99%

Section: Reactions Of C 60 With Aldehydes/ketonesmentioning

confidence: 99%

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Ferric perchlorate-mediated radical reactions of [60]fullerene

Wang

2012

Sci. China Chem.

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Fullerenes

Li¹,

Wang²

2013

Kirk-Othmer Encyclopedia of Chemical Technology

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Fullerenes are a class of three‐dimensional all‐carbon hollow molecules containing a conjugated n system and are sometimes referred to as the “third form of carbon”. Each fullerene Cn consists of an even number of carbon atoms and represents a closed‐cage structure with 12 pentagons and (n–20)/2 hexagons. The isolated pentagon rule is an important principle to determine the stability of fullerene cages. [60]Fullerene (C60) has a truncated icosahedral spherical structure with 20 hexagons and 12 pentagons. [70]Fullerene (C70) is a kiwi‐like ellipsoidal molecule and its structure contains an additional equatorial band of 10 carbons relative to that of C60. Fullerenes containing > 70 atoms are known as “higher fullerenes”. Unlike the other forms of carbon, fullerenes are soluble and thus can undergo a wide range of chemical reactions. The main chemical reactions of fullerenes are nucleophilic additions, cycloadditions, and radical additions. The hollow cavities of fullerenes can enclose a wide variety of atoms, molecules, or metal clusters, and the class of fullerenes are named as endohedral fullerenes. In addition, the replacement of one or more carbons of the fullerene cage by other non‐carbon atoms such as nitrogen can lead to heterofullerenes. Fullerene derivatives bearing electrondonor groups have been investigated because of the potential for conversion of light into electricity. Some alkali metal‐doped fullerenes show the interesting superconducting properties. Although fullerenes are insoluble in water, some derivatives are very soluble and this has led to investigations of biological properties.

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Straightforward and Versatile Synthesis of Fullerooxazoles from C₆₀ and Carboxamides through Radical Reactions under Mild Conditions

Takeda¹,

Enokijima²,

Nagamachi³

et al. 2012

Asian J Org Chem

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A direct synthetic method for producing oxazoline‐fused fullerenes, that is, fullerooxazoles, from [60] fullerene and readily available carboxamides by radical pathways has been developed. The method presented allows efficient access to a variety of fullerooxazoles with high functional compatibility under mild reaction conditions. Furthermore, systematic investigation of their properties, such as solubility, thermostability, and electrochemical behavior, was conducted.

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Synthesis of Fullerooxazoles: Novel Reactions of [60]Fullerene with Nitriles Promoted by Ferric Perchlorate

Cited by 96 publications

References 47 publications

Ferric perchlorate-mediated radical reactions of [60]fullerene

Ferric perchlorate-mediated radical reactions of [60]fullerene

Fullerenes

Straightforward and Versatile Synthesis of Fullerooxazoles from C₆₀ and Carboxamides through Radical Reactions under Mild Conditions

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Synthesis of Fullerooxazoles: Novel Reactions of [60]Fullerene with Nitriles Promoted by Ferric Perchlorate

Cited by 96 publications

References 47 publications

Ferric perchlorate-mediated radical reactions of [60]fullerene

Ferric perchlorate-mediated radical reactions of [60]fullerene

Fullerenes

Straightforward and Versatile Synthesis of Fullerooxazoles from C60 and Carboxamides through Radical Reactions under Mild Conditions

Contact Info

Product

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Straightforward and Versatile Synthesis of Fullerooxazoles from C₆₀ and Carboxamides through Radical Reactions under Mild Conditions