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 | |
| State | Published - May 21 1998 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Tetrahydrofuran, tetrahydropyran and oxepane formation by cobaloxime π-cation cyclizations
AU - Grubb, Lana M.
AU - Brown, Katherine A.
AU - Branchaud, Bruce
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
VL - 39
SP - 3447
EP - 3448
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 21
ER -