The lead tetraacetate oxidation of saturated aliphatic alcohols, with structures which do not permit 1,5-cyclization, gave tetrahydropyran derivatives in yields not exceeding 16%. The formation of a small amount of the rearranged ether, 2-ethyl-2-methyltetrahydrofuran, from 4,4-dimethyl-1-pentanol indicates that the cyclization reaction proceeds via an intermediate with carbonium ion character.
TY - JOUR
AU - Mihailovíć, Milhailo Lj.
AU - Čeković, Živorad M.
AU - Jeremić, Dragoslav
PY - 1965
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4628
AB - The lead tetraacetate oxidation of saturated aliphatic alcohols, with structures which do not permit 1,5-cyclization, gave tetrahydropyran derivatives in yields not exceeding 16%. The formation of a small amount of the rearranged ether, 2-ethyl-2-methyltetrahydrofuran, from 4,4-dimethyl-1-pentanol indicates that the cyclization reaction proceeds via an intermediate with carbonium ion character.
PB - Elsevier
T2 - Tetrahedron
T1 - Lead tetraacetate oxidation of saturated aliphatic alcohols-IV. The formation of six-membered cyclic ethers
VL - 21
IS - 10
SP - 2813
EP - 2821
DO - 10.1016/S0040-4020(01)98366-8
ER -
@article{
author = "Mihailovíć, Milhailo Lj. and Čeković, Živorad M. and Jeremić, Dragoslav",
year = "1965",
url = "https://cer.ihtm.bg.ac.rs/handle/123456789/4628",
abstract = "The lead tetraacetate oxidation of saturated aliphatic alcohols, with structures which do not permit 1,5-cyclization, gave tetrahydropyran derivatives in yields not exceeding 16%. The formation of a small amount of the rearranged ether, 2-ethyl-2-methyltetrahydrofuran, from 4,4-dimethyl-1-pentanol indicates that the cyclization reaction proceeds via an intermediate with carbonium ion character.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Lead tetraacetate oxidation of saturated aliphatic alcohols-IV. The formation of six-membered cyclic ethers",
volume = "21",
number = "10",
pages = "2813-2821",
doi = "10.1016/S0040-4020(01)98366-8"
}
Mihailovíć, M. Lj., Čeković, Ž. M.,& Jeremić, D. (1965). Lead tetraacetate oxidation of saturated aliphatic alcohols-IV. The formation of six-membered cyclic ethers.
Tetrahedron
Elsevier., 21(10), 2813-2821.
https://doi.org/10.1016/S0040-4020(01)98366-8
Mihailovíć ML, Čeković ŽM, Jeremić D. Lead tetraacetate oxidation of saturated aliphatic alcohols-IV. The formation of six-membered cyclic ethers. Tetrahedron. 1965;21(10):2813-2821
Mihailovíć Milhailo Lj., Čeković Živorad M., Jeremić Dragoslav, "Lead tetraacetate oxidation of saturated aliphatic alcohols-IV. The formation of six-membered cyclic ethers" Tetrahedron, 21, no. 10 (1965):2813-2821,
https://doi.org/10.1016/S0040-4020(01)98366-8 .
