Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols

Bew, Sean P. ORCID: https://orcid.org/0000-0002-9087-9463, Stephenson, G. Richard ORCID: https://orcid.org/0000-0003-1487-9178, Rouden, Jacques, Martinez-Lozano, Luis A. and Seylani, Haseena (2013) Malonic acid half oxyesters and thioesters: Solvent-free synthesis and DFT analysis of their enols. Organic Letters, 15 (15). pp. 3805-3807. ISSN 1523-7060

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Abstract

A much improved synthetic route to malonic acid half thioesters (MAHTs) and oxyesters (MAHOs), the easy incorporation of deuterium labeling expecially in MAHTs, and an unexpectedly large difference in enolization chemistry between MAHTs and MAHOs are reported. Density functional theory calculations explore the origins of this difference and identify an additional MAHT molecular orbital which increases delocalization between sulfur and the enol in both cisoid and transoid forms.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: Pure Connector
Date Deposited: 02 Feb 2015 13:58
Last Modified: 07 Oct 2022 00:40
URI: https://ueaeprints.uea.ac.uk/id/eprint/51968
DOI: 10.1021/ol400804b

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