Issue 96, 2014
From the journal:

RSC Advances

Oxidative rearrangement of malondialdehyde: substrate scope and mechanistic insights†

Xin Yu,a   Zheng Liu,b   Zilei Xia,c   Zhigao Shen,c   Xixian Pan,a   Hui Zhang*a  and  Weiqing Xie*b  

* Corresponding authors

a Department of Chemistry, School of Science & Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China
E-mail: yehao7171@163.com

b State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
E-mail: xiewq@sioc.ac.cn

c State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China

Abstract

A novel oxidative rearrangement of malondialdehyde was described. Under the effect of H2O2, malondialdehyde smoothly transferred to carboxylic acid with C–C bond cleavage in good to excellent yields. Mechanistic studies showed that this reaction proceeded via the formation of a 1,2-dioxolane intermediate, followed by concert C–C, O–O, C–H bond cleavage and a hydride shift.

Graphical abstract: Oxidative rearrangement of malondialdehyde: substrate scope and mechanistic insights

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Article information

DOI
https://doi.org/10.1039/C4RA11237G
Article type
Communication
Submitted
26 Sep 2014
Accepted
16 Oct 2014
First published
16 Oct 2014

RSC Adv., 2014,4, 53397-53401

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Oxidative rearrangement of malondialdehyde: substrate scope and mechanistic insights

X. Yu, Z. Liu, Z. Xia, Z. Shen, X. Pan, H. Zhang and W. Xie, RSC Adv., 2014, 4, 53397 DOI: 10.1039/C4RA11237G

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