Vibration milling, high-speed

Solid-state [4 + 2] cycloaddition of fullerene C60 with condensed aromatics using a high-speed vibration milling technique [100]... 

A spectacular solid-state [2 + 2] dimerization reaction of Cso was discovered by Komatsu et al.[ul When a mixture of C6o and potassium cyanide is intimately ground by high-speed vibration milling, an unusual addition-elimination reaction involving the cyanide adduct 37 ensues which joins two ful-lerene moieties to afford the Q20 dimer 38 (Scheme 10). Presumably, the cyclodimerization involves... 

Ikeda A, Hayashi K, Konishi T, Kikuchi J (2004) Solubilization and debundling of purified single-walled carbon nanotubes using solubilizing agents in an aqueous solution by high-speed vibration milling technique. Chem. Commun. 1334-1335. 

Abstract More than a decade has passed since fullerenes became avaUahle to researchers in almost all fields of science. The explosive development of study on the chemical functionalization of fullerenes has led to a wide variety of fullerene derivatives. However, most of these reactions have been carried out in the liquid phase, and curiously enough the solid-state reaction (or solid-solid reaction) of fullerenes has been developed only in recent years. This chapter focuses on the solid-state reaction of fullerenes, particularly the reaction which was conducted under what is called high-speed vibration milling conditions. It will be shown how this reaction technique is pertinent for the creation of fullerene derivatives with novel structures, and how efficient this method is for certain reactions compared with the liquid-phase reaction. 

Recently, a solvent-free variation was found to be equally effective. The inorganic base Na2C03 was utilized to replace the organic base DBU in a mechanochemical reaction under high-speed vibration milling conditions [37]. The yields with diethyl bromomalonate are in the range 40-50%. 

The solid-state reaction of cyanide with using the high speed vibration mill ... 

Another Cgo dimer connected by a silicon bridge and a single bond was prepared by Fujiwara and Komatsu using the high-speed vibration milling technique (Scheme 8.10). They also proposed the mechanism for the formation of Ceo dimer, which involves the ionic reaction between dichlorodiphenylsilane and Cgo radical anion formed by one-electron transfer from lithium (Li) and radical coupling of the two Ceo cages. 

The solvent-free reactions of fullerenes and A -alkylglycines with aldehydes using high-speed vibration milling have been successfully accomplished by Wang and co-workers. Various fulleropyrrolidines were obtained in good yields by reactions of Ceo with aldehydes and V-methylglycine (Scheme 8.12). °... 

The Bingel reaction of diethyl bromomalonate and Ceo, under the mechano-chemical high-speed vibration milling conditions, produced cyclopropanated Ceo in good yield. However, the reactions of diethyl malonate and ethyl acetoacetate with Ceo afforded 1,4-bisadduct and dihydrofuran-fused Ceo derivative, respectively (Scheme 8.13). ... 

Wang and co-workers also evaluated the reactivity of 9-substituted anthracene in Diels-Alder reactions with fullerene. Corresponding adducts were prepared in high yields under solvent-free conditions using the high-speed vibration milling technique (Scheme 8.14). ... 

Keywords Michael reaction, azachalcone, high-speed vibration milling... 

Solvent-free reaction of 1 with C60 in the presence of Mn(OAc)3 2H20 and CAN under high-speed vibration milling conditions afforded dihydrofuran-fused[60]fullerene. CAN was a better oxidant than Mn(OAc)3 2H20 in these mechanochemical reactions (05MI1327). 

The coupling of Cso molecules through [2 + 2] cycloaddition to give C120 (13.4) can be achieved by a solid state reaction that involves high-speed vibration milling of Cgo in the presence of catalytic amounts of KCN. When heated at 450 K for a short period, the C120 molecule dissociates into Cgo-... 

A solvent-free self-assembly offullerene Cjq using high-speed vibration milling has been described [19]. This simple, efficient, and green pathway to the synthesis of a supramolecular complex in the solid state opened a new avenue for the application of solventless reactions. 

A) A home-built high-speed vibration mill and (B) the interior of the mill. The grinding jar is inserted into the tilted metal tubing in front. (By courtesy of Prof. Yasujiro Murata, Kyoto University.) (C) In HSVM the jar oscillates in different planes as opposed to mixer mills. 

Fan W, Gao J, Jia J, Han L, Sheng W, Li Y. Solvent-free synthesis of p-enamino ketones (esters) under high-speed vibration milling (HSVM) condition. Chin J Org Chem 2010 30 1732-6. 

Li Y-J, Cao Y-W, Xu F-S, Fang W-M, Yu W-B, Jia J-H, Gao J-R. Solvent and catalyst free azo-Michael addition under high-speed vibration milling. Sci China Chem 2012 55 1252-6. 

Reproduced from Estdvez V, Villacampa M, Menpndez JC. Three-component access to pyrroles promoted by the CAN-silver nitrate system under high-speed vibration milling conditions a generalization of the hantzsch pyrrole synthesis. Chem Common 2013 49 591-3, with permission from the Royal Society of Chemistry. 

Custom-made high-speed vibration mill, stainless steel, 60Hz, Ceo.reactant base 1 1.5 1.5. Isolated yields. 

Wang and coworkers have found that solvent-free mechanochemical reaction of [60]fnllerene with phenylhydrazine hydrochlorides 59a-e in the presence of sodinm carbonate nnder high-speed vibration-milling conditions afforded l-aryl-1,2-dihydro[60]fnllerenes 60a-e (Scheme 7.16) [31]. Noteworthy difference in comparison to solntion conditions is l-(4-nitrophenyl)-l,2-dihydro[60]fullerene 60e which conld not be obtained in the liquid-phase reaction. When excess sodium nitrite was employed to replace sodinm carbonate, fullerotriazoline 61 was formed. 

Wang G-W, Zhang T-H, Hao E-H, Jiao L-J, Murata Y, Komatsu K. Solvent-free reactions of fuUerenes and IV-alkylglycines with and without aldehydes under high-speed vibration milling. Tetrahedron 2003 59 55-60. 

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