The University of Southampton
University of Southampton Institutional Repository

Formation of a zwitterionic enolate from tetramethylthiourea and dimethyl acetylenedicarboxylate

Formation of a zwitterionic enolate from tetramethylthiourea and dimethyl acetylenedicarboxylate
Formation of a zwitterionic enolate from tetramethylthiourea and dimethyl acetylenedicarboxylate
A zwitterionic tetrahydrothiophen-3-one derivative containing the enolate of a -keto ester located in the ring and a tetramethylamidinium group in a side chain is formed from tetramethylthiourea and dimethyl acetylenedicarboxylate by a surprising rearrangement reaction. Low-temperature X-ray crystallography shows weak intramolecular coordination of an enolate O atom by the amidinium group (OC: 2.608 angstrom) and also a 1,5 SO short contact (2.706 angstrom) due to electron delocalisation in a cis-sulfanylacrylate grouping
1434-193X
6621-6624
Wannebroucq, Amélie
2740a411-14e9-4d4d-8e3c-975b7e47cf1b
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Wallis, John D.
bc777046-08c0-40bf-9cfd-3a69481bb06a
Wannebroucq, Amélie
2740a411-14e9-4d4d-8e3c-975b7e47cf1b
Pitak, Mateusz B.
eeb6a00f-2291-4376-830f-d30dfd607ed1
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Wallis, John D.
bc777046-08c0-40bf-9cfd-3a69481bb06a

Wannebroucq, Amélie, Pitak, Mateusz B., Coles, Simon J. and Wallis, John D. (2014) Formation of a zwitterionic enolate from tetramethylthiourea and dimethyl acetylenedicarboxylate. European Journal of Organic Chemistry, 2014 (30), 6621-6624. (doi:10.1002/ejoc.201402807).

Record type: Article

Abstract

A zwitterionic tetrahydrothiophen-3-one derivative containing the enolate of a -keto ester located in the ring and a tetramethylamidinium group in a side chain is formed from tetramethylthiourea and dimethyl acetylenedicarboxylate by a surprising rearrangement reaction. Low-temperature X-ray crystallography shows weak intramolecular coordination of an enolate O atom by the amidinium group (OC: 2.608 angstrom) and also a 1,5 SO short contact (2.706 angstrom) due to electron delocalisation in a cis-sulfanylacrylate grouping

This record has no associated files available for download.

More information

Published date: October 2014
Organisations: Chemistry

Identifiers

Local EPrints ID: 371989
URI: http://eprints.soton.ac.uk/id/eprint/371989
ISSN: 1434-193X
PURE UUID: a8dee13b-3937-4d53-b0b0-430693b85877
ORCID for Mateusz B. Pitak: ORCID iD orcid.org/0000-0002-3680-7100
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 24 Nov 2014 11:24
Last modified: 15 Mar 2024 03:01

Export record

Altmetrics

Contributors

Author: Amélie Wannebroucq
Author: Mateusz B. Pitak ORCID iD
Author: Simon J. Coles ORCID iD
Author: John D. Wallis

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×