C602- chemistry:: C60 adducts bearing two ester, carbonyl, or alcohol groups

被引：31

作者：

Allard, E ^{[1
]}

Delaunay, J ^{[1
]}

Cousseau, J ^{[1
]}

机构：

[1] Univ Angers, UMR CNRS 6501, Lab Ingn Mol & Mat Organ, F-49045 Angers 01, France

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 13期

关键词：

D O I：

10.1021/ol034545k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of activated halo compounds XCH2-A (X = Br, I; A = ester, ketone) with C-60(2-) anion give rise to C-60(CH2-A)(2) adducts (major products) along with unexpected methanofullerenes; C-60>CH-A and monosubstituted dihydrofullerenes C-60(H)(CH2-A) (minor products). Methanofullerenes are shown to come from side reactions with X2CH-A traces.

引用

页码：2239 / 2242

页数：4

共 18 条

[1] Easy access to unprecedented mixed functionalized dihydrofullerenes C60RH and C60RR′:: the C602- anion route [J].

Allard, E ;

Cheng, FY ;

Chopin, S ;

Delaunay, J ;

Rondeau, D ;

Cousseau, J .

NEW JOURNAL OF CHEMISTRY, 2003, 27 (02) :188-192

[2] Novel C60-based building blocks derived from C602- anion [J].

Allard, E ;

Delaunay, J ;

Cheng, FY ;

Cousseau, J ;

Ordúna, J ;

Garín, J .

ORGANIC LETTERS, 2001, 3 (22) :3503-3506

[3] Chemical generation and reactivity of C602-.: High-yield and regioselective alkylation of [60, Ih] fullerene [J].

Allard, E ;

Rivière, L ;

Delaunay, J ;

Dubois, D ;

Cousseau, J .

TETRAHEDRON LETTERS, 1999, 40 (40) :7223-7226

[4] REACTION OF BUCKMINSTERFULLERENE WITH ORTHO-QUINODIMETHANE - A NEW ACCESS TO STABLE C60 DERIVATIVES [J].

BELIK, P ;

GUGEL, A ;

SPICKERMANN, J ;

MULLEN, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (01) :78-80

[5] CYCLOPROPYLATION OF FULLERENES [J].

BINGEL, C .

CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (08) :1957-1959

[6] A new route for the selective synthesis of [6,6]-methanofullerenes. Electrosynthesis of C(61)HCMe(3) and C61HCN [J].

Boulas, PL ;

Zuo, YH ;

Echegoyen, L .

CHEMICAL COMMUNICATIONS, 1996, (13) :1547-1548

[7] ELECTROCHEMICAL STUDIES OF THE PROTONATION OF C-60- AND C-60(2-) [J].

CLIFFEL, DE ;

BARD, AJ .

JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (33) :8140-8143

[8]

Da Ros T, 1999, CHEM COMMUN, P663

[9] Formation of C60 adducts with two different alkyl groups via combination of electron transfer and SN2 reactions [J].

Fukuzumi, S ;

Suenobu, T ;

Hirasaka, T ;

Arakawa, R ;

Kadish, KM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9220-9227

[10]

Hirsch A, 1994, CHEM FULLERENES

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