Full Text:   <2328>

CLC number: O622.6

On-line Access: 

Received: 2004-06-25

Revision Accepted: 2004-07-24

Crosschecked: 0000-00-00

Cited: 1

Clicked: 4885

Citations:  Bibtex RefMan EndNote GB/T7714

-   Go to

Article info.
Open peer comments

Journal of Zhejiang University SCIENCE A 2004 Vol.5 No.10 P.1175-1179

http://doi.org/10.1631/jzus.2004.1175


A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system


Author(s):  ZHANG Yong-min, LIN Mao-qin, YU Yong-ping

Affiliation(s):  Department of Chemistry, Zhejiang University, Hangzhou 310028, China; more

Corresponding email(s):   yminzhang@mail.hz.zj.cn

Key Words:  Grignard reagent, Cp2TiCl2-catalyzed, &alpha, -diketone, &beta, -diketone, Reduction


Share this article to: More

ZHANG Yong-min, LIN Mao-qin, YU Yong-ping. A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system[J]. Journal of Zhejiang University Science A, 2004, 5(10): 1175-1179.

@article{title="A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system",
author="ZHANG Yong-min, LIN Mao-qin, YU Yong-ping",
journal="Journal of Zhejiang University Science A",
volume="5",
number="10",
pages="1175-1179",
year="2004",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2004.1175"
}

%0 Journal Article
%T A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system
%A ZHANG Yong-min
%A LIN Mao-qin
%A YU Yong-ping
%J Journal of Zhejiang University SCIENCE A
%V 5
%N 10
%P 1175-1179
%@ 1869-1951
%D 2004
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2004.1175

TY - JOUR
T1 - A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system
A1 - ZHANG Yong-min
A1 - LIN Mao-qin
A1 - YU Yong-ping
J0 - Journal of Zhejiang University Science A
VL - 5
IS - 10
SP - 1175
EP - 1179
%@ 1869-1951
Y1 - 2004
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2004.1175


Abstract: 
&alpha;-diketone%29&ck%5B%5D=abstract&ck%5B%5D=keyword'>-diketones and &beta;-diketone%29&ck%5B%5D=abstract&ck%5B%5D=keyword'>-diketones react with grignard reagents in the presence of a catalytic amount of Cp2TiCl2 to yield &alpha;-ketols and corresponding ketones respectively. Sulfoxides can be deoxygenated by Cp2TiCl2/Al system. The possible mechanisms are also discussed.

Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article

Reference

[1] Gao, Y., Sato, F., 1995. On the mechanism of titanocene-dichloride-catalyzed hydromagnesiation of alkynes with alkyl Grignard reagents. J. Chem. Soc., Chem. Commun., 659-661.

[2] Nugent, W., Rajanbabu, T., 1988. Transition-metal-centered radicals in organic synthesis. Titanium (III)-induced cyclization of epoxy olefins. J. Am. Chem. Soc., 110:8561-8562.

[3] Sato, F., Kobayashi, Y., 1990. Hydromagnesiation reaction of propargylic alcohols: (E)-3-pentyl-2-nonene-1,4-diol from 2-octyn-1-ol. Org. Synth., 69:106-107.

[4] Sato, F., Jinbo, T., Sato, M., 1980. Cp2TiCl2-catalyzed Grignard reactions: reactions with ketones and aldehydes. Tetrahedron Lett., 21:2171-2174.

[5] Xu, X., Huang, X., 1997. A new method for the reductive cleavage of Se-Se bond by titanocene dichloride isobutylmagnesium bromide system and its application in synthesis of selenoester. Synth. Commun., 27:3797.

[6] Yu, Y.P., Zhang, Y.M., 1999. A novel reduction of β-ketoester with Cp2TiCl2/i-PrMgBr system. Synth. Commun., 29:243-247.

[7] Yu, Y.P., Zhang, Y.M., 1995. The reduction sulfoxides and active halides with Cp2TiCl2/Sm system. Synth. Commun., 25:1825-1830.

[8] Zhang, Y.M., Hu, Z.Y., 1988. (NMCp)2TiCl2-catalyzed reduction of aliphatic, aromatic, and α, β-unsaturated ketones by Grignard reagent. Tetrahedron Lett., 29:4113-4114.

[9] Zhang, Y.M., Jiang, J.L., Chen, Y., 1987. Cp2TiCl2-catalyzed reactions of Grignard reagents with isocyanates, formation of carboxamide with rearranged carbonskeleton. Terahedron Lett., 28:3815-3816.

[10] Zhang, Y.M., Jiang, J.L., Zhang, Z.X., 1988. Cp2TiCl2-catalyzed reactions of Grignard reagents with isocyanates, formation of reduction-coupling product of isocyanates. Tetrahedron Lett., 29:651-652.

Open peer comments: Debate/Discuss/Question/Opinion

<1>

Please provide your name, email address and a comment





Journal of Zhejiang University-SCIENCE, 38 Zheda Road, Hangzhou 310027, China
Tel: +86-571-87952783; E-mail: cjzhang@zju.edu.cn
Copyright © 2000 - 2022 Journal of Zhejiang University-SCIENCE