Full Text:   <1939>

CLC number: O622.6

On-line Access: 

Received: 2005-10-24

Revision Accepted: 2005-11-30

Crosschecked: 0000-00-00

Cited: 1

Clicked: 4153

Citations:  Bibtex RefMan EndNote GB/T7714

-   Go to

Article info.
1. Reference List
Open peer comments

Journal of Zhejiang University SCIENCE B 2006 Vol.7 No.3 P.198-201

http://doi.org/10.1631/jzus.2006.B0198


Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4


Author(s):  Li Xue, Zhang Yong-Min

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

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

Key Words:  Azo compounds, Reduction, Amides, Sm/TiCl4


Li Xue, Zhang Yong-Min. Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4[J]. Journal of Zhejiang University Science B, 2006, 7(3): 198-201.

@article{title="Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4",
author="Li Xue, Zhang Yong-Min",
journal="Journal of Zhejiang University Science B",
volume="7",
number="3",
pages="198-201",
year="2006",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2006.B0198"
}

%0 Journal Article
%T Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4
%A Li Xue
%A Zhang Yong-Min
%J Journal of Zhejiang University SCIENCE B
%V 7
%N 3
%P 198-201
%@ 1673-1581
%D 2006
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.2006.B0198

TY - JOUR
T1 - Study on the reactions of azo compounds with acyl halides mediated by Sm/TiCl4
A1 - Li Xue
A1 - Zhang Yong-Min
J0 - Journal of Zhejiang University Science B
VL - 7
IS - 3
SP - 198
EP - 201
%@ 1673-1581
Y1 - 2006
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.2006.B0198


Abstract: 
amides can be obtained in good to excellent yield by sm/TiCl4 mediated reductive cleavage of N=N bond in azo compounds and successive acylation in one pot. It offers an alternative method for the synthesis of amides from very simple starting materials directly.

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

Reference

[1] Banik, B.K., 2002. Samarium metal in organic synthesis. Eur. J. Org. Chem., 2002(15):2431-2444.

[2] Chen, J., Zhang, Y., 2004. Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives. J. Zhejiang Univ. SCI, 5(2):218-221.

[3] Donaruma, L.G., Heldt, W.Z., 1960. The Beckmann rearrangement. Org. React., 11:2-36.

[4] Gawley, R.E., 1988. The Beckmann reactions: rearrangement, elimination-additions, fragmentations, and rearrangement-cyclizations. Org. React., 35:14-24.

[5] Gilchrist, T.L., 1991. Reductions of N=N, N-N, N-O and O-O bonds. In: Trost, B.M., Fleming, I. (Eds.), Comprehensive Organic Synthesis. Pergamon Press, Oxford, 8:381-402.

[6] Girard, P., Namy, J.L., Kagan, H.B., 1980. Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents. J. Am. Chem. Soc., 102(8):2693-2698.

[7] Krief, A., Laval, A.M., 1999. Coupling of organic halides with carbonyl compounds promoted by SmI2, the Kagan reagent. Chem. Rev., 99(3):745-778.

[8] Li, Z.F., Zhang, Y.M., 2000. Facile synthesis of amidines via intermolecular reductive coupling of nitriles with azobenzene promoted by samarium diiodide. Chin. Chem. Lett., 11:495-498.

[9] Molander, G.A., 1998. Diverse methods for medium ring synthesis. Acc. Chem. Res., 31(10):603-609.

[10] Molander, G.A., Harris, C.R., 1996. Sequencing reactions with samarium (II) iodide. Chem. Rev., 96(1):307-338.

[11] Molander, G.A., Harris, C.R., 1998. Sequenced reactions with samarium (II) iodide. Tetrahedron, 54(14):3321-3354.

[12] Movassagh, B., Meibodi, F., Sobhani, S., 2002. Facile reparation of amides from thioamides by ceric ammonium nitrate. Indian J. of Chem., 41B:1296-1298.

[13] Souppe, J., Danon, L., Namy, J.L., Kagan, H.B., 1983. Some organic reactions promoted by samarium diiodide. J. Organomet. Chem., 250(1):227-236.

[14] Zhang, Y.M., Lin, M.Q., Yu, Y.P., 2004. A novel reduction of diketones with i-RMgBr catalyzed by Cp2Ti2Cl2 and deoxygenation of sulfoxides by Cp2Ti2Cl2/Al system. J. Zhejiang Univ. SCI, 5:1175-1179.

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