Synlett 2018; 29(15): 1983-1988
DOI: 10.1055/s-0037-1610235
letter
© Georg Thieme Verlag Stuttgart · New York

Exploration of the Role of Double Schiff Bases as Catalytic Intermediates in the Knoevenagel Reaction of Furanic Aldehydes: Mechanistic Considerations

a   Research Group Biopolymers/Green Chemistry, Centre of Expertise BioBased Economy, Avans University of Applied Science, Lovensdijkstraat 61, 4818 AJ Breda, The Netherlands   Email: jam.vanschijndel@avans.nl
b   Department of Chemical Engineering and Chemistry, Lab of Chemical Reactor Engineering/Polymer Reaction Engineering, Eindhoven University of Technology, Den Dolech 2, 5600 MB Eindhoven, The Netherlands
,
Luiz Alberto Canalle
a   Research Group Biopolymers/Green Chemistry, Centre of Expertise BioBased Economy, Avans University of Applied Science, Lovensdijkstraat 61, 4818 AJ Breda, The Netherlands   Email: jam.vanschijndel@avans.nl
,
Dennis Molendijk
a   Research Group Biopolymers/Green Chemistry, Centre of Expertise BioBased Economy, Avans University of Applied Science, Lovensdijkstraat 61, 4818 AJ Breda, The Netherlands   Email: jam.vanschijndel@avans.nl
,
Jan Meuldijk
b   Department of Chemical Engineering and Chemistry, Lab of Chemical Reactor Engineering/Polymer Reaction Engineering, Eindhoven University of Technology, Den Dolech 2, 5600 MB Eindhoven, The Netherlands
› Author Affiliations

The authors are grateful for the financial support from Netherlands Organization for Scientific Research (NWO) (grant 023.007.020 awarded to Jack van Schijndel).
Further Information

Publication History

Received: 12 April 2018

Accepted after revision: 17 July 2018

Publication Date:
13 August 2018 (online)


Preview

Abstract

This paper presents mechanistic considerations on an efficient, green, and solvent-free Knoevenagel procedure for the chemical transformation of furanic aldehydes into their corresponding α,β-unsaturated compounds. In the proposed mechanism furanic aldehydes react with ammonia, released from ammonium salts, to form a catalytically active double Schiff base. The catalytic intermediates involved in the condensation step are characterized.

Supporting Information