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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 01: 104 - 112

DOI: https://doi.org/10.6023/cjoc1106302

Articles

Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines

  • FU Jian-Hua ,
  • WANG Chao-Yang ,
  • HUO Jing-Pei ,
  • TAN Yue-He ,
  • ZENG Rong-Hua
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  • School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2011-06-30

  Revised date: 2011-08-29

  Online published: 2011-09-21

Supported by

Project supported by the the National Natural Science Foundation of China (No. 20772035), the Natural Science of Foundation of Guangdong Provine (No. 5300082) and the 3rd Talents Special Funds of Guangdong Higher Education (No. [2011]431).

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Abstract

Using KF as catalyst and tetrahydrofuran as solvent, 5-alkyloxy-3,4-dihalo-2(5H)-furanones was reacted with several aliphatic amines. The chemical structures and absolute configurations of the products were confirmed via rotation, UV-Vis, IR, 1H NMR, 13C NMR, MS techniques, elemental analysis and X-ray single crystal diffraction. Thirteen new normal products β-amino-2(5H)-furanones were obtained via the tandem Michael addition-elimination reaction as anticipated in most cases. However, the reaction between the larger steric dicyclohexyl amine and 5-alkyloxy-3,4-dihalo-2(5H)-furanones yielded four new abnormal products, (E)-alkyl 2-halo-4-dicyclohexylamino-4-oxobut-2-enoate. The possible mechanism for the formation of 2(5H)-furanone ring-opening products involving in the rearrangement reaction was proposed.

Key words： 5-alkoxy-3,4-dihalo-2(5H)-furanone; aliphatic saturated secondary amine; tandem Michael addition-elinmination reaction; β-amino-2(5H)-furanone; ring-opening rearrangement reaction

Cite this article

FU Jian-Hua , WANG Chao-Yang , HUO Jing-Pei , TAN Yue-He , ZENG Rong-Hua . Research on the Reaction of 5-Alkyloxy-3,4-dihalo-2(5H)- furanones with Aliphatic Amines[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 104 -112 . DOI: 10.6023/cjoc1106302

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