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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",
journal="Journal of Zhejiang University Science A",
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pages="218-221",
year="2004",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.2004.0218"
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%A CHEN Jue
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%J Journal of Zhejiang University SCIENCE A
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%@ 1869-1951
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%I Zhejiang University Press & Springer
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A1 - CHEN Jue
A1 - ZHANG Yong-min
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SP - 218
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%@ 1869-1951
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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

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[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.

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