150493-27-9Relevant articles and documents
Synthesis and reactions of 2,2-[60]fullerenoalkanoyl chlorides
Tada, Tomoyuki,Ishida, Yasuhiro,Saigo, Kazuhiko
, p. 1633 - 1639 (2006)
2,2-[60]Fullerenoalkanoyl chlorides (1a-d) were easily and securely prepared from the corresponding 2,2-[60]fullerenoalkanoic acids (2a-d) by the reaction with thionyl chloride in an unusual mixed solvent, CH 2Cl2/dioxane. The characterization of 1a-d by 1H and 13C NMR, FT-IR, and MALDI-TOF-MASS was conducted for the first time. The 2,2-[60]fullerenoalkanoyl chlorides thus obtained were readily converted to the corresponding amides and esters in moderate to excellent yields by the condensation with amines and alcohols, respectively. Upon applying the condensation, [60]fullerene-biomolecule hybrids were easily prepared.
Synthesis of methano[60]fullerene derivatives: The fluoride ion-mediated reaction of [60]fullerene with silylated nucleophiles
Hino, Tetsuo,Kinbara, Kazushi,Saigo, Kazuhiko
, p. 5065 - 5067 (2001)
A new reaction of [60]fullerene with silylated nucleophiles is described. The cyclopropanation of [60]fullerene with silylated nucleophiles, such as silyl ketene acetals, silyl ketene thioacetals, and silyl enol ethers, derived from α-halo carbonyl compounds, smoothly proceeded in the presence of KF/18-crown-6 to give the corresponding methano[60]fullerene derivatives in moderate to good yields.
Catalytic [2+1]-cycloaddition of ethyl diazoacetate to fullerene [60]
Tuktarov,Akhmetov,Kamalov,Khalilov,Pudas,Ibragimov,Dzhemilev
, p. 1168 - 1174 (2009)
Cyclopropanation of C60-fullerene was performed with ethyl diazoacetate in the presence of Pd(PPh3)4 catalyst. A probable reaction mechanism is suggested.
176. Structures and Chemistry of Methanofullerenes: A Versatile Route into N--Substituted Amino Acids
Isaacs, Lyle,Diederich, Francois
, p. 2454 - 2464 (1993)
The reaction of C60 with oxadiazole 13 afforded the dimethoxymethanofullerene 7 in 32 percent yields as a 6-6-ring-bridged isomer with a closed transannular bond.A literature survey showed that all 6-6-ring-bridged methanofullerenes are ?-homoaromatic with a closed transannular bond (6-6-closed) and all 6-5-ring-bridged are ?-homoaromatic with an open transannular bond (6-5-open).The preference for 6-6-closed and 6-5-open structures is not due to substituent effects but is best explained with the conservation in these isomers of the favorable bonding seen in C60 with higher double- bond character at 6-6-bonds and higher single-bond character at 6-5-bonds.Reaction of C60 with diazo diester 15 gave the fullerene diester 14 which was hydrolyzed with BBr3 in benzene to the methanofullerenecarboxylic acid 10, a versatile synthon for the preparation of amphiphilic fullerene derivatives.Treatment of 10 with alcohols and amino acid esters under DCC coupling conditions afforded the esters 5 and 17 and the amino-acid derivatives 11 and 12, respectively.
C602- chemistry: C60 adducts bearing two ester, carbonyl, or alcohol groups
Allard, Emmanuel,Delaunay, Jacques,Cousseau, Jack
, p. 2239 - 2242 (2003)
(Matrix presented) Reactions of activated halo compounds XCH2-A (X = Br, I; A = ester, ketone) with C602- anion give rise to C60(CH2-A)2 adducts (major products) along with unexpected metha
[60]Fullerenoacetyl chloride as a versatile precursor for fullerene derivatives: Efficient ester formation with various alcohols
Ito, Hiroshi,Tada, Tomoyuki,Sudo, Masafumi,Ishida, Yasuhiro,Hino, Tetsuo,Saigo, Kazuhiko
, p. 2643 - 2645 (2003)
(Matrix presented) [60]Fullerenoacetyl chloride, one of the reactive derivatives of [60]fullerenoacetic acid, was isolated and identified for the first time. This acid chloride was easily synthesized in good yield from tert-butyl [60]fullerenoacetate through two steps. In the presence of 4-(dimethylamino)-pyridine as a base, the acid chloride smoothly reacted with various alcohols under mild conditions to give the corresponding esters including [60]fullerene-biomolecule hybrids in moderate to high yields.
CuBr/PMDETA-mediated reactions of [60]fullerene with active halides: Preparation of methano[60]fullerene derivatives
Yang, Hai-Tao,Tian, Zong-Yong,Ruan, Xiao-Jiao,Zhang, Min,Miao, Chun-Bao,Sun, Xiao-Qiang
supporting information, p. 4918 - 4922 (2012/11/13)
An efficient protocol for the synthesis of methano[60]fullerene derivatives linked with a single electron-withdrawing group has been developed through one-step reaction of [60]fullerene with active halides mediated by CuBr/pentamethyldiethylenetriamine. M