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


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Senol H., Bayrak C., Menzek A., Şahin E., Karakus M.

TETRAHEDRON, vol.72, pp.2587-2592, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 72
  • Publication Date: 2016
  • Doi Number: 10.1016/j.tet.2016.03.094
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2587-2592
  • Bezmialem Vakıf University Affiliated: Yes

Abstract

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.