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Received: 2004-06-25

Revision Accepted: 2004-07-24

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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


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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.

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author="ZHANG Yong-min, LIN Mao-qin, YU Yong-ping",
journal="Journal of Zhejiang University Science A",
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pages="1175-1179",
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publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2004.1175"
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%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
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%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2004.1175

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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
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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

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[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.

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