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

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

Fingerprint

Keywords

Carbonium ions
Cobalt and compounds
Cyclization
Ethers

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Grubb, L. M., Brown, K. A., & Branchaud, B. P. (1998). Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime π-cation cyclizations. Tetrahedron Letters, 39(21), 3447-3448. https://doi.org/10.1016/S0040-4039(98)00601-7

@article{4fd69876778b4d3c84a0d1f4bfdf2b05,

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

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.",

keywords = "Carbonium ions, Cobalt and compounds, Cyclization, Ethers",

author = "Grubb, {Lana M.} and Brown, {Katherine A.} and Branchaud, {Bruce P.}",

year = "1998",

month = may

day = "21",

doi = "10.1016/S0040-4039(98)00601-7",

language = "English (US)",

volume = "39",

pages = "3447--3448",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "21",

}

TY - JOUR

T1 - Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime π-cation cyclizations

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

UR - http://www.scopus.com/inward/record.url?scp=0032555027&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032555027&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(98)00601-7

DO - 10.1016/S0040-4039(98)00601-7

M3 - Article

AN - SCOPUS:0032555027

VL - 39

SP - 3447

EP - 3448

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 21

ER -

Access to Document

10.1016/S0040-4039(98)00601-7