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Journal of Zhejiang University SCIENCE A 2004 Vol.5 No.2 P.218-221

http://doi.org/10.1631/jzus.2004.0218


Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives


Author(s):  CHEN Jue, ZHANG Yong-min

Affiliation(s):  Ningbo Institute of Technology, Zhejiang University, Ningbo 315104, China; more

Corresponding email(s):   chenjue@hkem.com

Key Words:  Metallic samarium, Catalyzed by iodine, 1, 1-dicyanoalkenes, Reductive cyclodimerization, Cyclopentene derivatives


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CHEN Jue, ZHANG Yong-min. Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives[J]. Journal of Zhejiang University Science A, 2004, 5(2): 218-221.

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author="CHEN Jue, ZHANG Yong-min",
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pages="218-221",
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publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2004.0218"
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T1 - Reductive cyclodimerization of arylmethylidenemalononitriles promoted by samarium and catalytic amount of iodine: facile synthesis of cyclopentene derivatives
A1 - CHEN Jue
A1 - ZHANG Yong-min
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PB - Zhejiang University Press & Springer
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DOI - 10.1631/jzus.2004.0218


Abstract: 
Samarium and a catalytic amount of iodine were used to obtain functionalized cyclopentenes by reductive dimerization followed by intramolecular cyclization of 1,1-dicyanoalkenes under mild conditions.

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

Reference

[1] Cook, A.G., 1969. Enamines: Their Synthesis, Structure and Reaction. Marcel Dekker, New York.

[2] Fan, X.S., Zhang, Y.M., 2001. Reductive cyclodimerization ofα,β-unsaturated ketones promoted by AlCl3/Sm system: a facile synthesis of 2-aroyl-1,3,3-triaryl cyclopentanol derivatives.Chin. J. Chem.,19(6):616-619(in Chinese).

[3] Helmers, R., Kaiser, W., 1971. Ueber eine alkylierende retro-thorpe-reaktion.Tetrahedron Lett.,12:3853-3855.

[4] Huang, Y., Zhang, Y.M., 1997. Preparation of disulfides by reduction of sodium alkyl thiosulfates with metallic samarium and catalytic amount of iodine.Synth. Commun.,27(6):1043-1047.

[5] Huang, Y., Zhang, Y.M., Wang, Y.L., 1997. Facile reduction of azides to the corresponding amines with metallic samarium and catalytic amount of iodine.Tetrahedron Lett.,38(6):1065-1066.

[6] Molander, G.A., 1992. Application of lanthanide reagents in organic synthesis.Chem. Rev.,92(1):29-68.

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

[8] Ogawa, A., Nanke, T., Takami, N., Takam, Y., 1994. Enhanced reducing ability by the combination of SmI2 and Sm metal in the reduction of alkyl halides.Chem. Lett., (2):379-380.

[9] Seitz, G., Monnighoff, H., 1971. Die thorpe-ziegler-cyclisi-erung zur synthese von substituierten cyclopenta thiophene.Tetrahedron Lett.,12:4889-4890.

[10] Stork, G., Brizzolaro, A., Landesman, H., Szmuszkovicz, J., Terrel, R., 1963. The enamine alkylation and acylation of carbonyl compounds.J. Am. Chem. Soc.,85:207-222.

[11] Yanada, R., Negoro, N., Okaniwa, M., Ibuka, T., 1999. Diastereoselective allylation and albylation of optically active imines with metallic samarium and a catalytic amount of iodide.Tetrahedron,55(49):13947-13956.

[12] Zhong, W.H., Zhang, Y.M., 2000. Samarium diiodide mediated simultaneous reduction of nitro group and azide group in o-nitrophenylazide: a new access to 2,3-dihydro-1H-1,5-benzodiazepines.J. Chem. Res., (8):532-534.

[13] Zhou, L.H., Zhang, Y.M., 1997. A novel cyclodimerization of Arylidenecyanoacetate promoted by samarium diiodide.Tetrahedron Lett.,38(46):8063-8066.

[14] Zhou, L.H., Zhang, Y.M., 1998. A novel reductive cyclization of arylmethyllidenemalononitrile promoted by samarium diiodide.J. Chem. Soc., Perkin Trans.I, (15):2399-2402.

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