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Awheda, Ismail; Saygili, Nezire; Garner, A. Christopher; Wallis, John D.
{ "DOI": "10.1039/c3ra41074a", "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.", "author": [ { "family": "Awheda", "given": " Ismail" }, { "family": "Saygili", "given": " Nezire" }, { "family": "Garner", "given": " A. Christopher" }, { "family": "Wallis", "given": " John D." } ], "container_title": "RSC ADVANCES", "id": "15111", "issue": "47", "issued": { "date-parts": [ [ 2013, 1, 1 ] ] }, "page": "24997-25009", "title": "Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack", "type": "article-journal", "volume": "3" }
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