Issue 87, 2017

Synthetic routes for a variety of halogenated (chiral) acetic acids from diethyl malonate

Abstract

Chiral halomethane is the smallest stable molecule with a single asymmetric C-atom and halogenated acetic acids often serve as precursors. We focus on a synthetic route to synthesise chiral halogenated acetic acids with F, Cl, Br, and H/D isotopic substitution at the α-C-atom starting from diethyl malonate. This reactant is easily available, cheap and allows the obtainment of target acids in a few reaction steps with great versatility. Among all of the possible fully halogenated acetic acids (more than one hundred, which are, in principle, accessible by this route), there are only a small number of chiral halogenated acetic acids, which have been synthesized following the devised synthetic route.

Graphical abstract: Synthetic routes for a variety of halogenated (chiral) acetic acids from diethyl malonate

Associated articles

Supplementary files

Article information

Article type
Paper
Submitted
01 Sep 2017
Accepted
18 Nov 2017
First published
07 Dec 2017
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2017,7, 55434-55440

Synthetic routes for a variety of halogenated (chiral) acetic acids from diethyl malonate

M. R. Mazenauer, S. Manov, V. M. Galati, P. Kappeler and J. Stohner, RSC Adv., 2017, 7, 55434 DOI: 10.1039/C7RA09727A

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