Cycloaddition reaction of spiro[2.4]hepta-4,6-dien-1-ylmethanol and PTAD: a new rearrangement

SENOL H., BAYRAK C., MENZEK A., ŞAHİN E., KARAKUS M.

TETRAHEDRON, cilt.72, sa.20, ss.2587-2592, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 72 Sayı: 20
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1016/j.tet.2016.03.094
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2587-2592
  • Atatürk Üniversitesi Adresli: Evet

Özet

Reaction of spiro[2.4]hepta-4,6-dien-1-ylmethanol (3) with phenyltriazolinedione (PTAD) gave 4-phenyl-1-[(3aR(S),6S(R))-1a, 2,3a, 6-tetrahydro-1H-cyclopenta[b]cyclopropa[c]furan-6-yl]-1,2,4-triazolidine-3,5-dione (7) via a novel rearrangement. The structure of this rearranged product was determined by spectroscopic methods and by experimentation. Influences of functional groups on the rearrangement and formation of 7 were discussed. (C) 2016 Elsevier Ltd. All rights reserved.