Issue 19, 2009
From the journal:

Chemical Communications

Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid: dual activated 1,2-hydride shift mechanism by protonated Al(OH)3 species†

Takashi Ohshima,*a   Yoshihiro Yamamoto,*b   Usaji Takaki,b   Yoshihisa Inoue,b   Takuya Saeki,b   Kenji Itou,b   Yusuke Maegawa,a   Takanori Iwasakia  and  Kazushi Mashima*a  

* Corresponding authors

a Department of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Japan
E-mail: ohshima@chem.es.osaka-u.ac.jp, mashima@chem.es.osaka-u.ac.jp
Fax: +81-6-6850-6249
Tel: +81-6-6850-6246

b Catalyst Science Laboratory, Mitsui Chemicals, Inc., 580-32 Nagaura, Sodegaura-city, Chiba 299-0265, Japan
E-mail: Yoshihiro.Yamamoto@mitsui-chem.co.jp
Fax: +81-438-64-2382
Tel: +81-438-64-2300

Abstract

Density functional theory calculations demonstrate that Al(III)-catalyzed conversion of glyoxal to glycolic acid proceeds via a 7-membered dual Lewis acid-hydrogen bonding activation transition state of the 1,2-hydride shift, rather than the previously proposed 5-membered metal-alkoxide chelate activation transition state.

Graphical abstract: Theoretical study of Al(iii)-catalyzed conversion of glyoxal to glycolic acid: dual activated 1,2-hydride shift mechanism by protonated Al(OH)3 species

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Article information

DOI
https://doi.org/10.1039/B902729G
Article type
Communication
Submitted
10 Feb 2009
Accepted
03 Mar 2009
First published
26 Mar 2009

Chem. Commun., 2009, 2688-2690

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Theoretical study of Al(III)-catalyzed conversion of glyoxal to glycolic acid: dual activated 1,2-hydride shift mechanism by protonated Al(OH)3 species

T. Ohshima, Y. Yamamoto, U. Takaki, Y. Inoue, T. Saeki, K. Itou, Y. Maegawa, T. Iwasaki and K. Mashima, Chem. Commun., 2009, 2688 DOI: 10.1039/B902729G

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