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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

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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: 18 Feb 2021 16:53

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