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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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{
  "@context": "https://schema.org/", 
  "@id": 15111, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "affiliation": "Nottingham Trent Univ, Sch Sci & Technol, Nottingham NG11 8NS, England", 
      "name": "Awheda, Ismail"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Hacettepe Univ, Fac Pharm, Dept Basic Pharmaceut Sci, TR-06100 Ankara, Turkey", 
      "name": "Saygili, Nezire"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Nottingham Trent Univ, Sch Sci & Technol, Nottingham NG11 8NS, England", 
      "name": "Garner, A. Christopher"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Nottingham Trent Univ, Sch Sci & Technol, Nottingham NG11 8NS, England", 
      "name": "Wallis, John D."
    }
  ], 
  "datePublished": "2013-01-01", 
  "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.", 
  "headline": "Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack", 
  "identifier": 15111, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack", 
  "url": "https://aperta.ulakbim.gov.tr/record/15111"
}
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