Issue 3, 2015
From the journal:

Green Chemistry

Zemplén transesterification: a name reaction that has misled us for 90 years†

Bo Ren,a   Meiyan Wang,b   Jingyao Liu,b   Jiantao Ge,a   Xiaoling Zhanga  and  Hai Dong*a  

* Corresponding authors

a School of Chemistry & Chemical Engineering, Huazhong University of Science & Technology, Luoyu Road 1037, Wuhan, P.R. China
E-mail: hdong@mail.hust.edu.cn
Fax: (+86) 27-87793242

b Institute of Theoretical Chemistry, State Key Laboratory of Theoretical and Computational Chemistry, Jilin University, Liutiao Road 2, Changchun, P. R. China

Abstract

We demonstrated that using NaOH and NaOMe in methanol for deacylation are identical, indicating that the Zemplén condition has been misleading us for almost 90 years. The traditional base-catalyzed mechanism cannot be used to explain our results. We propose that H-bond complexes play key roles in the base-catalyzed process, explaining why deacylation in methanol can be catalyzed by hydroxide.

Graphical abstract: Zemplén transesterification: a name reaction that has misled us for 90 years

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Article information

DOI
https://doi.org/10.1039/C4GC02006E
Article type
Communication
Submitted
15 Oct 2014
Accepted
21 Nov 2014
First published
24 Nov 2014

Green Chem., 2015,17, 1390-1394

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Zemplén transesterification: a name reaction that has misled us for 90 years

B. Ren, M. Wang, J. Liu, J. Ge, X. Zhang and H. Dong, Green Chem., 2015, 17, 1390 DOI: 10.1039/C4GC02006E

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