Synthesis of pyrrolidine ring-fused metallofullerene derivatives

被引：38

作者：

Lu, X ^{[1
]}

He, XR ^{[1
]}

Feng, L ^{[1
]}

Shi, ZJ ^{[1
]}

Gu, ZN ^{[1
]}

机构：

[1] Peking Univ, Dept Chem, Beijing 100871, Peoples R China

来源：

TETRAHEDRON | 2004年 / 60卷 / 16期

基金：

中国国家自然科学基金;

关键词：

azomethine ylides; metallofullerene pyrrolidines; 1,3-dipolar addition;

D O I：

10.1016/j.tet.2004.02.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The azomethine ylide generated from the reaction of sarconsine and formaldehyde adds to Gd@C-82 to give the mono- through octo-adducts, while the direct interaction of sarcosine with Gd@C-82 yields only the mono-adduct, which is characterized by HPLC, MALDI-TOF MS, UV-Vis-NIR and FT-IR. The reaction mechanism for this reaction is proposed to be a 1,3-dipolar addition. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：3713 / 3716

页数：4

相关论文

共 14 条

[1] EXOHEDRAL ADDUCTS OF LA-AT-C-82 [J].

AKASAKA, T ;

KATO, T ;

KOBAYASHI, K ;

NAGASE, S ;

YAMAMOTO, K ;

FUNASAKA, H ;

TAKAHASHI, T .

NATURE, 1995, 374 (6523) :600-601

[2] Absorption spectra of metallofullerenes M@C82 of lanthanoids [J].

Akiyama, K ;

Sueki, K ;

Kodama, T ;

Kikuchi, K ;

Ikemoto, I ;

Katada, M ;

Nakahara, H .

JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (31) :7224-7226

[3]

[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3

[4] First soluble M@C60 derivatives provide enhanced access to metallofullerenes and permit in vivo evaluation of Gd@C60[C(COOH)2]10 as a MRI contrast agent [J].

Bolskar, RD ;

Benedetto, AF ;

Husebo, LO ;

Price, RE ;

Jackson, EF ;

Wallace, S ;

Wilson, LJ ;

Alford, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5471-5478

[5] Chemical modification of Tb@C82 by copper(I)-catalyzed cycloadditions [J].

Feng, L ;

Zhang, XM ;

Yu, ZP ;

Wang, JB ;

Gu, ZN .

CHEMISTRY OF MATERIALS, 2002, 14 (10) :4021-+

[6]

FENG L, UNPUB

[7] Synthesis of fullerene amino acid derivatives by direct interaction of amino acid ester with C-60 [J].

Gan, LB ;

Zhou, DJ ;

Luo, CP ;

Tan, HS ;

Huang, CH ;

Lu, MJ ;

Pan, JQ ;

Wu, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :1954-1961

[8] A symmetric derivative of the trimetallic nitride endohedral metallofullerene, Sc3N@C80 [J].

Iezzi, EB ;

Duchamp, JC ;

Harich, K ;

Glass, TE ;

Lee, HM ;

Olmstead, MM ;

Balch, AL ;

Dorn, HC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (04) :524-525

[9] Lutetium-based trimetallic nitride endohedral metallofullerenes: New contrast agents [J].

Iezzi, EB ;

Duchamp, JC ;

Fletcher, KR ;

Glass, TE ;

Dorn, HC .

NANO LETTERS, 2002, 2 (11) :1187-1190

[10] ADDITION OF AZOMETHINE YLIDES TO C-60 - SYNTHESIS, CHARACTERIZATION, AND FUNCTIONALIZATION OF FULLERENE PYRROLIDINES [J].

MAGGINI, M ;

SCORRANO, G ;

PRATO, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9798-9799