Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack

Awheda, I., Saygili, N., Garner, A.C. ORCID: 0000-0003-2488-0623 and Wallis, J.D. ORCID: 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
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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