Unexpected reactions of [60]fullerene involving tertiary amines and insight into the reaction mechanisms

被引：57

作者：

Wang, Guan-Wu

Chen, Xiao-Ping

Cheng, Xin

机构：

[1] Hefei Natl Lab Phys Sci Microscale, Hefei, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2006年 / 12卷 / 27期

关键词：

60]fullerene; amino acids; cycloaddition; reaction mechanisms; tertiary amines;

D O I：

10.1002/chem.200600575

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermal reactions of [60]fullerene with amino acid ester hydrochlorides and triethylamine in o-dichlorobenzene at reflux afforded pyrrolidinofullerene derivatives containing the CH,CH moiety and originating from triethylamine through an unusual C-N bond cleavage. Detailed investigation of these thermal reactions resulted in the discovery of unprecedented reactions between C-60 and tertiary amines and of reactions Of C-60 with tertiary amines and aldehydes, giving cyclopentafullerene derivatives with high stereoselectivity. Plausible reaction mechanisms for the product formation involving the uncommon C-N bond cleavage of tertiary amines were proposed on the basis of extensive experimental results.

引用

页码：7246 / 7253

页数：8

共 50 条

[41] A facile access to [60]fullerene-fused δ-lactones: unexpected reaction pathway of benzenediazonium-2-carboxylates controlled by organic bases
Wang, Guan-Wu
Zhu, Bo
CHEMICAL COMMUNICATIONS, 2009, (13) : 1769 - 1771
[42] Metal-Free Synthesis of N-Alkyl-2,5-Unsubstituted/Monosubstituted Fulleropyrrolidines: Reaction of [60]Fullerene with Paraformaldehyde and Amines
Li, Yun-Fei
Zhang, Duo
Wang, Hui-Juan
Li, Fa-Bao
Sun, Liang
Liu, Li
Liu, Chao-Yang
Asiri, Abdullah M.
Alamry, Khalid A.
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05): : 2922 - 2932
[43] NMR Speciation of Aqueous MAPA, Tertiary Amines, and Their Blends in the Presence of CO2: Influence of pKa and Reaction Mechanisms
Perinu, Cristina
Bernhardsen, Ida M.
Pinto, Diego D. D.
Knuutila, Hanna K.
Jens, Klaus-J.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2018, 57 (05) : 1337 - 1349
[44] Synthesis and characterization of divalent organolanthanide-fullerene adducts Cp2LnC60 (Ln = Yb, Sm): First example of insertion reaction involving cyclopentadienyl and fullerene
Nanjing Univ, Nanjing, China
Fullerene Sci Technol, 6 (1087-1096):
[45] Synthesis and characterization of divalent organolanthanide-fullerene adducts Cp2LnC60 (Ln = Yb,Sm):: First example of insertion reaction involving cyclopentadienyl and fullerene
Wang, SW
Wei, XW
Zhou, KY
Xu, Z
FULLERENE SCIENCE AND TECHNOLOGY, 1998, 6 (06): : 1087 - 1096
[46] Synthesis and characterization of divalent organolanthanide-fullerene adducts Cp(2)LnC(60) (Ln=Yb, Sm): First example of insertion reaction involving cyclopentadienyl and fullerene.
Wang, SW
Wei, XW
Qi, L
Xu, Z
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 238 - INOR
[47] PHOTOINDUCED INTERMOLECULAR AND INTRAMOLECULAR ELECTRON-TRANSFER REACTIONS OF [60]FULLERENE AND A TERTIARY AMINE - FORMATION OF THE CYCLOADDUCT N-ETHYL-TRANS-2',5'-DIMETHYLPYRROLIDINO[3',4'/1,2][60]FULLERENE
LAWSON, GE
KITAYGORODSKIY, A
MA, B
BUNKER, CE
SUN, YP
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (21) : 2225 - 2226
[48] Pyrolysis involving n-hexadecane, water and minerals: Insight into the mechanisms and isotope fractionation for water-hydrocarbon reaction
He, Kun
Zhang, Shuichang
Mi, Jingkui
Zhang, Wenlong
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS, 2018, 130 : 198 - 208
[49] An Unexpected Reaction: [2 + 1] Cycloaddition of [60]Fullerene with 4,4,5,5-Tetramethylimidazolidine-2-Thione and DL-Valine
Xu, J.-H.
Li, Y.-L.
Zheng, D.-G.
Yang, J.-K.
Tetrahedron Letters, 38 (37):
[50] Application of 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole in analysis: Fluorescent dyes and unexpected reaction with tertiary amines
Annenkov, Vadim V.
Verkhozina, Olga N.
Shishlyannikova, Tatyana A.
Danilovtseva, Elena N.
ANALYTICAL BIOCHEMISTRY, 2015, 486 : 5 - 13

← 1 2 3 4 5 →