Preparation of cyclohexene-d10 by H/D-exchange reaction

被引:19
作者
Ishibashi, Kenichi [1 ]
Matsubara, Seijiro [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan
关键词
D O I
10.1246/cl.2007.724
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Preparation of fully deuterium-labeled cyclohexene by H/ D-exchange reaction was performed efficiently in the presence of ruthenium catalyst under irradiation of microwaves. The reaction proceeds via a repetition of hydroruthenation and beta-elimination.
引用
收藏
页码:724 / 725
页数:2
相关论文
共 29 条
[21]   Phosphane-free rhodium catalyst in an anionic micellar system for [4+2] annulation of dienynes [J].
Motoda, D ;
Kinoshita, H ;
Shinokubo, H ;
Oshima, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (14) :1860-1862
[22]   Efficient C-H/C-D exchange reaction on the alkyl side chain of aromatic compounds using heterogeneous Pd/C in D2O [J].
Sajiki, H ;
Aoki, F ;
Esaki, H ;
Maegawa, T ;
Hirota, K .
ORGANIC LETTERS, 2004, 6 (09) :1485-1487
[23]   ACTIVATION OF SATURATED-HYDROCARBONS BY METAL-COMPLEXES IN SOLUTION [J].
SHILOV, AE ;
SHTEINMAN, AA .
COORDINATION CHEMISTRY REVIEWS, 1977, 24 (2-3) :97-143
[24]   Ruthenium catalyzed deuterium labelling of α-carbon in primary alcohol and primary/secondary amine in D2O [J].
Takahashi, M ;
Oshima, K ;
Matsubara, S .
CHEMISTRY LETTERS, 2005, 34 (02) :192-193
[25]   HIGH-TEMPERATURE AND DILUTE ACID (HTDA) PROCEDURE AS A GENERAL METHOD OF REPLACING AROMATIC HYDROGEN BY DEUTERIUM .2. [J].
WERSTIUK, NH ;
KADAI, T .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (11) :2169-2171
[26]   PROTIUM DEUTERIUM-EXCHANGE OF CYCLIC AND ACYCLIC ALKENES IN DILUTE ACID-MEDIUM AT ELEVATED-TEMPERATURES [J].
WERSTIUK, NH ;
TIMMINS, G .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (02) :530-533
[27]  
Yamamoto M, 2006, HETEROCYCLES, V67, P353
[28]   H-D exchange reaction on benzene ring of polystyrene in hydrothermal deuterium oxide with platinum(IV) oxide catalyst [J].
Yamamoto, M ;
Yokota, Y ;
Oshima, K ;
Matsubara, S .
CHEMICAL COMMUNICATIONS, 2004, (15) :1714-1715
[29]   DEUTERATION OF EXTREMELY WEAK ORGANIC-ACIDS BY ENHANCED ACID-BASE REACTIVITY IN SUPERCRITICAL DEUTEROXIDE SOLUTION [J].
YAO, J ;
EVILIA, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) :11229-11233