Reaction of p-Nitrophenylsulfonylacetate with α,β-Unsaturated Esters Under Solid-Liquid Phase Transfer Conditions

Chem. J. Chinese Universities ›› 1995, Vol. 16 ›› Issue (9): 1410.

• Articles • Previous Articles Next Articles

Reaction of p-Nitrophenylsulfonylacetate with α,β-Unsaturated Esters Under Solid-Liquid Phase Transfer Conditions

CHEN Wen-Hua, ZHANG Zheng, XU Xiao-Qing

Department of Chemistry, Nanjing University, Nanjing, 210008

Received:1994-10-25 Revised:1995-02-08 Online:1995-09-24 Published:1995-09-24

Abstract

Abstract: The reaction of p-nitrophenylsulfonylacetate with α,β-unsaturated esters under solid-liquid phase transfer conditions (K₂CO₃/DMF/TEBA) gave the unexpected Michael addition-rearrangement products, For example, the reaction of pnitrophenylsulfonylacetate with methyl methacrylate resulted in the formation of 2-methyl-2-(p-nitrophenyl) glutarate, presumably through the Michael adduct, which might rearrange to an intermediate, furtherlose sulfur dioxide and then led to the final product.

Key words: p-Nitrophenylsulfonylacetate, α,β-unsaturated ester, Solid-liquid phase-transfer catalysis, Michael addition

TrendMD:

CHEN Wen-Hua, ZHANG Zheng, XU Xiao-Qing . Reaction of p-Nitrophenylsulfonylacetate with α,β-Unsaturated Esters Under Solid-Liquid Phase Transfer Conditions[J]. Chem. J. Chinese Universities, 1995, 16(9): 1410.

[1]	LIU Qian, LI Wenhong, QIU Zhaolai, LI Yuan. Michael Addition of Aminothiophenols to α,β-Unsaturated Ketones with High Steric Hindrance Catalyzed by CeCl₃·7H₂O-NaI^† [J]. Chem. J. Chinese Universities, 2014, 35(3): 538.
[2]	QIU Zhao-Lai, LI Wen-Hong, ZHU Hai-Fei, LIU Qian, LI Yuan. Synthesis, Crystal Structure and Antifungal Activities of 3-(CH₂)_nCO₂C₂H₅-1,5-Benzothiazepines [J]. Chem. J. Chinese Universities, 2013, 34(3): 579.
[3]	GAO Zhao-Bo, QIU Xue-Peng, GUO Hai-Quan, KANG Chuan-Qing, GAO Lian-Xun . Michael Addition Reaction of Thiophenol with Intramolecular Hydrogen Bond in Aqueous Medium [J]. Chem. J. Chinese Universities, 2004, 25(8): 1471.
[4]	LI Xue-Qiang, CHEN Qinq-Hua . Synthesis and Structure of the Chiral Dialkyl Phosphonate Derivatives [J]. Chem. J. Chinese Universities, 2001, 22(10): 1677.
[5]	LI Xue-Qiang, GONG Bo-Lin, WANG Feng-Rong, CHEN Qing-Hua, WANG Zhi-Dan . Michael Addition-elimination Reactions of Chiral-5-Alkoxy-3,4-dihalo-2(5H)-Furanones in DMF [J]. Chem. J. Chinese Universities, 2001, 22(1): 78.
[6]	HUANG Hui, CHEN Qing-Hua. Synthesis of 3-Bicyclo[3.3.0]octene Derivatives Containing Multiple Chiral Centers [J]. Chem. J. Chinese Universities, 1999, 20(9): 1384.
[7]	WANG En-Si, SHEN Jia-Cong, Henry N. C. WONG. Synthetic Studies on-2-Substituted-1,7-dioxaspiro[4.4]nonan-8-one [J]. Chem. J. Chinese Universities, 1997, 18(7): 1054.
[8]	XU Zhang-Huang, HUANG Jin-Xia, LI Yan, CHEN Zu-Xing, GAO Ming-Zhang. Stereoselective Synthesis of (+)-Eldanolide Using a Chiral Sulfoxide [J]. Chem. J. Chinese Universities, 1995, 16(9): 1391.
[9]	JIANG Dong-Lin, ZHANG Yi-Feng, SHEN Zhi-Quan. Studies on High Permselective Gas Separation Membrane of Sulfur Dioxide(Ⅲ)──Michael Addition Reaction of Vinyl Sulfoxide with Poly(vinyl alcohol) and Structure Characterization [J]. Chem. J. Chinese Universities, 1994, 15(1): 150.
[10]	LIU Guang-Jian, ZHANG Zheng, WANG Yu-Liang, ZHOU Wei-Qing, ZHANG Li-Kang, BAI Ya-Luo . Studies on Reactions of Sulfur-containing Carbanions and Their Applications (Ⅶ) ——Synthesis of 4,4-disubstituted1,7-Difunctional Compounds [J]. Chem. J. Chinese Universities, 1993, 14(5): 638.

Reaction of p-Nitrophenylsulfonylacetate with α,β-Unsaturated Esters Under Solid-Liquid Phase Transfer Conditions

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 10

Recommended Articles

Metrics

Comments