Rapid [3,3] sigmatropic rearrangements of allylic thiono chloroformates

ZAİM Ö.

Tetrahedron Letters, cilt.40, sa.46, ss.8059-8062, 1999 (SCI-Expanded, Scopus) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 40 Sayı: 46
  • Basım Tarihi: 1999
  • Doi Numarası: 10.1016/s0040-4039(99)01693-7
  • Dergi Adı: Tetrahedron Letters
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8059-8062
  • Anahtar Kelimeler: Alcohols, Rearrangements, Thiocarbamate, Thiocarbonyl
  • Trakya Üniversitesi Adresli: Evet

Özet

Treatment of allylic alcohols with thiophosgene and pyridine gives thiolo chloroformates directly at room temperature, presumably via very rapid [3,3] sigmatropic rearrangements of thiono chloroformates. Synthesis of allyl thiono chloroformate from allyl alcohol, sodium hydride and thiophosgene at low temperature and warming up to room temperature supports this finding.