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Citation: CHEN Wen-Hua, ZHANG Zheng. Synthesis of 2-Arylglutarate[J]. Chinese Journal of Applied Chemistry, ;2007, 24(8): 961-964. shu

Synthesis of 2-Arylglutarate

CHEN Wen-Hua ^a,, ,
ZHANG Zheng ^b

1.
a Department of Applied Chemistry, Changzhou Vocation College of Engineering and Technology, Changzhou 213164;
2.
b Department of Chemistry, Nanjing University, Nanjing

Corresponding author: CHEN Wen-Hua,
Received Date: 1 September 2006
Available Online: 8 February 2007

2-Arylglutarates with high yields (73%~87%) were prepared by addition-rearrangement reactions of phenylsulfonylacetates containing 4-nitro or 2-nitro with α,β-unsaturated esters under K₂CO₃-TEBA phase transfer catalyst conditions.The effects of substistution groups at the phenyl ring of reactant-arylsulfonylacetates on the addition-rearrangement reaction were examined.Arylsulfonylacetate containing 4-nitro or 2-nitro at the phenyl ring was found to carry out the addition-rearrangement reaction to form 2-arylglutarates under K₂CO₃-TEBA phase transfer catalyst conditions.The mechanism is proposed that the Michael adduct reactions of arylsulfonylacetates with α,β-unsaturated esters resulted in the Michael adducts,which might rearrange to the inter mediate through intramolecular nucleophilic substitution,which might further lose sulfur dioxide and then led to 2-arylglutarates.The Michael adduct reactions of arylsulfonylacetates containing electron-donating groups (for example:methyl) or weakly absorbing groups (for example:chloro) at 4-position or 2-position of the phenyl ring with α,β-unsaturated esters normally resulted in 2-arylsulfonylacetates.
- arylglutarate,
- arylsulfonylacetate,
- α,β-unsatutated ester,
- rearrangement reaction
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