Awheda, I, Saygili, N, Garner, AC ORCID: https://orcid.org/0000-0003-2488-0623 and Wallis, JD ORCID: https://orcid.org/0000-0001-7259-8783, 2013. Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack. RSC Advances, 3 (47), pp. 24997-25009. ISSN 2046-2069
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Abstract
The cyclic thionocarbamate of alaninol undergoes nucleophilic attack by sulfur nucleophiles at 5-C to give 1-thiopropyl-2-amine derivatives when derivatised on nitrogen with a Boc group. Iodide under microwave conditions causes a rearrangement to the isomeric thiazolidinone, while "hard" nucleophiles react at the thione group to yield a variety of product types by subsequent C–N or C–O cleavage. X-ray crystallography studies showed that the N-Boc group reduces delocalisation of electron density from nitrogen into the thione group, and thus promotes activation of the ring to nucleophilic attack.
Item Type: | Journal article |
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Publication Title: | RSC Advances |
Creators: | Awheda, I., Saygili, N., Garner, A.C. and Wallis, J.D. |
Publisher: | Royal Society of Chemistry |
Date: | 2013 |
Volume: | 3 |
Number: | 47 |
ISSN: | 2046-2069 |
Identifiers: | Number Type 10.1039/C3RA41074A DOI |
Rights: | © Royal Society of Chemistry 2013 |
Divisions: | Schools > School of Science and Technology |
Record created by: | EPrints Services |
Date Added: | 09 Oct 2015 10:02 |
Last Modified: | 09 Jun 2017 13:17 |
URI: | https://irep.ntu.ac.uk/id/eprint/6749 |
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