Selective electrochemical retro-cycloaddition reaction of pyrrolidinofullerenes

被引：54

作者：

Lukoyanova, Olena

Cardona, Claudia M.

Altable, Margarita

Filippone, Salvatore

Domenech, Angel Martin

Martin, Nazario

Echegoyen, Luis

机构：

[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ, E-28040 Madrid, Spain

[2] Clemson Univ, Dept Chem, Clemson, SC 29630 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 44期

关键词：

azomethine ylides; cycloaddition; electrochemistry; fullerenes; retro reactions;

D O I：

10.1002/anie.200602431

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Going retro: Controlled-potential electrolysis (CPE) is employed as a synthetic tool in the selective removal of addends from fullerene adducts. Reductive CPE has been extensively used in the retro-cyclo-propanation of fullerenes without affecting pyrrolidine addends also present. Now oxidative CPE for the selective removal of pyrrolidine addends in the presence of methano adducts is reported (see scheme). (Figure Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：7430 / 7433

页数：4

相关论文

共 29 条

[1] CYCLOPROPYLATION OF FULLERENES [J].

BINGEL, C .

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

[2] Redox characteristics of covalent derivatives of the higher fullerenes C70, C76, and C78 [J].

Boudon, C ;

Gisselbrecht, JP ;

Gross, M ;

Herrmann, A ;

Rüttimann, M ;

Crassous, J ;

Cardullo, F ;

Echegoyen, L ;

Diederich, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (31) :7860-7868

[3] 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

[4] The first fulleropyrrolidine derivative of Sc3N@C80:: Pronounced chemical shift differences of the geminal protons on the pyrrolidine ring [J].

Cardona, CM ;

Kitaygorodskiy, A ;

Ortiz, A ;

Herranz, MA ;

Echegoyen, L .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5092-5097

[5]

CHAMPS X, 1997, J CHEM SOC P1, P1595

[6] Electrochemical studies of seven regioisomers of tris[di(ethoxycarbonyl)methano][60]fullerene: Umpolung of regiochemistry in retro-bingel reactions and walk-on-the-sphere rearrangements [J].

Echegoyen, LE ;

Djojo, FD ;

Hirsch, A ;

Echegoyen, L .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4994-5000

[7] A simple isomeric separation of D5h and Ih Sc3N@C80 by selective chemical oxidation [J].

Elliott, B ;

Yu, L ;

Echegoyen, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) :10885-10888

[8] Preparation of [60]fullerene tris-malonate adducts by addend removal from higher adducts via the electrochemical retro-Bingel reaction [J].

Fender, NS ;

Nuber, B ;

Schuster, DI ;

Wilson, SR ;

Echegoyen, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (09) :1924-1928

[9] Thermally reversible C60-based donor-acceptor ensembles [J].

Herranz, MA ;

Martín, N ;

Ramey, J ;

Guldi, DM .

CHEMICAL COMMUNICATIONS, 2002, (24) :2968-2969

[10] FULLERENE CHEMISTRY IN 3 DIMENSIONS - ISOLATION OF 7 REGIOISOMERIC BISADDUCTS AND CHIRAL TRISADDUCTS OF C-60 AND DI(ETHOXYCARBONYL)METHYLENE [J].

HIRSCH, A ;

LAMPARTH, I ;

KARFUNKEL, HR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04) :437-438