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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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{
  "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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