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

Lana M. Grubb; Katherine A. Brown; Bruce P. Branchaud

doi:10.1016/S0040-4039(98)00601-7

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

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

Knight Cancer Institute

Research output: Contribution to journal › Article › peer-review

9 Scopus citations

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 language	English (US)
Pages (from-to)	3447-3448
Number of pages	2
Journal	Tetrahedron Letters
Volume	39
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(98)00601-7
State	Published - May 21 1998

Keywords

Carbonium ions
Cobalt and compounds
Cyclization
Ethers

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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.",

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AU - Grubb, Lana M.

AU - Brown, Katherine A.

AU - Branchaud, Bruce P.

PY - 1998/5/21

Y1 - 1998/5/21

N2 - 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.

AB - 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.

KW - Carbonium ions

KW - Cobalt and compounds

KW - Cyclization

KW - Ethers

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