Issue 13, 2016

N,N-Dicarboxymethyl hydrazine: an old but neglected reagent for chemoselective derivatization of carbonyl compounds

Abstract

N,N-Dicarboxymethyl hydrazine (DCMH) was found to be a chemoselective derivatization reagent of carbonyl compounds and its potential applications in organic synthesis was investigated for the first time. DCMH could be employed as a chemoselective protective reagent of aldehydes and gave the parent aldehydes in satisfactory yields. In proof-of-concept systems, DCMH could play the role of a scavenger to remove aldehydes in the presence of ketones. It was also used as a tagging reagent in the selective isolation of aldehyde from the complex mixture.

Graphical abstract: N,N-Dicarboxymethyl hydrazine: an old but neglected reagent for chemoselective derivatization of carbonyl compounds

Supplementary files

Article information

Article type
Paper
Submitted
23 Jan 2016
Accepted
02 Mar 2016
First published
04 Mar 2016

Org. Biomol. Chem., 2016,14, 3443-3449

N,N-Dicarboxymethyl hydrazine: an old but neglected reagent for chemoselective derivatization of carbonyl compounds

M. Zhen and Y. Peng, Org. Biomol. Chem., 2016, 14, 3443 DOI: 10.1039/C6OB00189K

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