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

Awheda, Ismail; Saygili, Nezire; Garner, A. Christopher; Wallis, John D.


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  <dc:creator>Awheda, Ismail</dc:creator>
  <dc:creator>Saygili, Nezire</dc:creator>
  <dc:creator>Garner, A. Christopher</dc:creator>
  <dc:creator>Wallis, John D.</dc:creator>
  <dc:date>2013-01-01</dc:date>
  <dc:description>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.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/15111</dc:identifier>
  <dc:identifier>oai:zenodo.org:15111</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>RSC ADVANCES 3(47) 24997-25009</dc:source>
  <dc:title>Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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