tetrabutylammonium bromide media aza-michael addition of 1,2,3,6-tetrahydrophthalimide to symmetrical fumaric esters and acrylic esters under solvent-free conditions四丁铵溴化媒体aza-michael的1、2、3,6-tetrahydrophthalimide对称反丁烯二酸的酯和丙烯酸酯在无溶剂的条件下.pdfVIP

Molecules 2010, 15, 7353-7362; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions Gholamhassan Imanzadeh *, Farzaneh Ahmadi, Mohammadreza Zamanloo and Yagoub Mansoori Department of Chemistry, College of Science, University of Mohaghegh Ardabili, 56199-11367, Ardabil, Iran Author to whom correspondence should be addressed; E-Mail: Imanzad2000@. Received: 19 September 2010; in revised form: 11 October 2010 / Accepted: 11 October 2010 / Published: 21 October 2010 ________________________________________________________________________________ Abstract : The aza-Michael addition of 1,2,3,6-tetrahydrophthalimide with symmetrical fumaric esters has been performed efficiently in a solvent-free system at 100 °C and using 1,4-diazabicyclo[2.2.2]octane (DABCO) as a base in the presence of tetrabutylammonium bromide (TBAB). The products were obtained in good to high yields within 2.5-7.0 h. This reaction worked well on linear alkyl fumarates and was not effective with nonlinear alkyl fumarates. Although the reaction was also applicable to acrylates such as n-butyl acrylate, methacrylates and crotonates were not suitable Michael acceptors for this reaction. Keyword: aza-Michael addition; 1,2,3,6-tetrahydrophthalimide; fumaric ester; tetrabutyl- ammonium bromide ________________________________________________________________________________ 1. Introd