Triazabicyclodecene:: An effective isotope exchange catalyst in CDCl3

被引：58

作者：

Sabot, Cyrille ^{[1
]}

Kumar, Kanduluru Ananda ^{[1
]}

Antheaume, Cyril ^{[1
]}

Mioskowski, Charles ^{[1
]}

机构：

[1] Univ Strasbourg 1, UMR 7175 LC1, CNRS, Lab Synthese Bioorgan,Serv Commun RMN, F-67401 Illkirch Graffenstaden, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 13期

关键词：

D O I：

10.1021/jo070307h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the first effective H/D exchange reaction with acidic substrates in CDCl3 at room temperature. The particularly mild reaction conditions involved (solvent, base, and temperature) allow the chemoselective deuteration of ketones over esters. An NMR study was conducted with the aim of rationalizing the results obtained in the presence of TBD as catalyst.

引用

收藏

页码：5001 / 5004

页数：4

相关论文

共 15 条

[1] A CORRELATION BETWEEN BETA-HYDROGEN ISOTOPE EFFECTS ON C-13 NMR CHEMICAL-SHIFTS IN UNSATURATED SYSTEMS AND THE STRENGTH OF HYPERCONJUGATIVE INTERACTIONS [J].

ARROWSMITH, CH ;

KRESGE, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (25) :7918-7920

[2] DEUTERIUM AND C-13 KINETIC ISOTOPE EFFECTS FOR THE ISOMERIZATION OF 5,5-DIMETHYLBICYCLO[2.1.0]PENT-2-ENE TO 5,5-DIMETHYLCYCLOPENTADIENE [J].

BALDWIN, JE ;

GHATLIA, ND .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3319-3325

[3]

BERGSON G, 1964, ACTA CHEM SCAND, V8, P2003

[4] Base-catalyzed deuterium and tritium labelling of 1-biphenyl-4-ylpropane-1,2-dione and deuteration of aryl methyl ketones [J].

Berthelette, C ;

Scheigetz, J .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2004, 47 (12) :891-894

[5]

FILIPPO JS, 1975, J ORG CHEM, V40, P782

[6] Microwave-assisted deuterium exchange reactions for the preparation of reactive intermediates [J].

Fodor-Csorba, K ;

Galli, G ;

Holly, S ;

Gäcs-Baitz, E .

TETRAHEDRON LETTERS, 2002, 43 (21) :3789-3792

[7] SYNTHESIS OF 1-DEUTERIATED AND 1,2,2'-DEUTERIATED DEOXYRIBOSE AND INCORPORATION INTO DEOXYRIBONUCLEOSIDES [J].

HODGE, RP ;

BRUSH, CK ;

HARRIS, CM ;

HARRIS, TM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1553-1564

[8] PHOTOCHEMISTRY OF 4-METHYLISOCHROMENE AND 1,5-HYDROGEN MIGRATION IN THE RESULTING ORTHO-XYLYLENE [J].

HORNBACK, JM ;

VADLAMANI, B .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (17) :3524-3525

[9]

KAEMPFEN U, 1989, Helvetica Chimica Acta, V72, P185

[10] Basicity of some organic superbases in acetonitrile [J].

Kovacevic, B ;

Maksic, ZB .

ORGANIC LETTERS, 2001, 3 (10) :1523-1526