Issue 20, 2014

Effective catalysis of imine metathesis by means of fast transiminations between aromatic–aromatic or aromatic–aliphatic amines

Abstract

This paper reports on a quantitative investigation of rates of amine–imine exchange reactions of primary amines with their benzylidene derivatives in organic solvents at room temperature. Exchange reactions involving aromatic–aromatic or aromatic–aliphatic amines were in all cases fast enough to allow their use in the effective catalysis of imine metathesis in the absence of acid and metal catalysis. Transiminations based on exchange between aromatic and aliphatic amines were retarded both by electron-donating and electron-withdrawing substituents in the para-position of the benzylidene moiety. This result was interpreted as arising from a change in the rate-determining step of the two-step transimination reaction.

Graphical abstract: Effective catalysis of imine metathesis by means of fast transiminations between aromatic–aromatic or aromatic–aliphatic amines

Supplementary files

Article information

Article type
Paper
Submitted
14 Jan 2014
Accepted
21 Mar 2014
First published
21 Mar 2014

Org. Biomol. Chem., 2014,12, 3282-3287

Author version available

Effective catalysis of imine metathesis by means of fast transiminations between aromatic–aromatic or aromatic–aliphatic amines

M. Ciaccia, S. Pilati, R. Cacciapaglia, L. Mandolini and S. Di Stefano, Org. Biomol. Chem., 2014, 12, 3282 DOI: 10.1039/C4OB00107A

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