Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime π-cation cyclizations

Lana M. Grubb, Katherine A. Brown, Bruce Branchaud

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Studies are reported on the cyclization of (ω-hydroxy-β-hydroxyalkyl)cobaloximes (1, 2 and 3) to form 5,6 and 7-membered ring cyclic ethers (4, 5 and 6). Reversible cyclization and eventual irreversible alkene decomplexation (to form 7, 8 and 9) varied as a function of ring size. The practical consequence is that cyclizations to form 5 and 6 membered rings are feasible whereas formation of a 7 membered ring is not.

Original languageEnglish (US)
Pages (from-to)3447-3448
Number of pages2
JournalTetrahedron Letters
Volume39
Issue number21
DOIs
StatePublished - May 21 1998
Externally publishedYes

Fingerprint

Cyclization
Cations
Cyclic Ethers
Alkenes
cobaloxime
tetrahydrofuran

Keywords

  • Carbonium ions
  • Cobalt and compounds
  • Cyclization
  • Ethers

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime π-cation cyclizations. / Grubb, Lana M.; Brown, Katherine A.; Branchaud, Bruce.

In: Tetrahedron Letters, Vol. 39, No. 21, 21.05.1998, p. 3447-3448.

Research output: Contribution to journalArticle

Grubb, Lana M. ; Brown, Katherine A. ; Branchaud, Bruce. / Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime π-cation cyclizations. In: Tetrahedron Letters. 1998 ; Vol. 39, No. 21. pp. 3447-3448.
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