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

Jack van Schijndel; Luiz Alberto Canalle; Dennis Molendijk; Jan Meuldijk

doi:10.1055/s-0037-1610235

Synlett, Table of Contents

Synlett 2018; 29(15): 1983-1988
DOI: 10.1055/s-0037-1610235

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

Jack van Schijndel *

^aResearch 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

^bDepartment 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

^aResearch 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

^aResearch 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

^bDepartment 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

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Abstract

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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.

Key words

furfural - 5-HMF - green Knoevenagel - catalytic intermediates - double Schiff base

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References

References and Notes
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