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

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Awheda I., SAYGILI N., Garner A. C., Wallis J. D.

RSC ADVANCES, cilt.3, sa.47, ss.24997-25009, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 3 Sayı: 47
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1039/c3ra41074a
  • Dergi Adı: RSC ADVANCES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.24997-25009
  • Hacettepe Üniversitesi Adresli: Evet

Özet

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.