Molecules 2010, 15(10), 7353-7362; doi:10.3390/molecules15107353
Article

Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions

Received: 19 September 2010; in revised form: 11 October 2010 / Accepted: 11 October 2010 / Published: 21 October 2010
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
Keywords: aza-Michael addition; 1,2,3,6-tetrahydrophthalimide; fumaric ester; tetrabutyl-ammonium bromide
PDF Full-text Download PDF Full-Text [184 KB, uploaded 18 June 2014 19:34 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

Imanzadeh, G.; Ahmadi, F.; Zamanloo, M.; Mansoori, Y. Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions. Molecules 2010, 15, 7353-7362.

AMA Style

Imanzadeh G, Ahmadi F, Zamanloo M, Mansoori Y. Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions. Molecules. 2010; 15(10):7353-7362.

Chicago/Turabian Style

Imanzadeh, Gholamhassan; Ahmadi, Farzaneh; Zamanloo, Mohammadreza; Mansoori, Yagoub. 2010. "Tetrabutylammonium Bromide Media Aza-Michael Addition of 1,2,3,6-Tetrahydrophthalimide to Symmetrical Fumaric Esters and Acrylic Esters under Solvent-Free Conditions." Molecules 15, no. 10: 7353-7362.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert