By means of lead tetra-acetate in refluxing benzene open-chain 1,2-, 1,3-, 1,4- and 1,5-hydroxy-ethers are mainly converted to the corresponding five-membered or six-membered cylic products. Thus, 2-alkoxy-1-ethanols afford 2-substituted 1,3-dioxolanes in 50-53% yield and 4-ethoxy-1-butanol gives 2-ethoxytetrahydrofuran in 52% yield; 3-alkoxy-1-propanols are oxidized to the corresponding 2-substituted 1,3-dioxans in 26-40% yield and 5-ethoxy-1-pentanol cyclizes to 2-ethoxytetrahydropyran in 46% yield. 2-Phenoxyethanol undergoes ring closure to 1,4-benzodioxan in 15% yield.
Keywords:
acyclic hydroxy-ethers / lead tetra-acetate / synthesis / ring closure / cyclisation
TY - JOUR
AU - Mihailović, Milhailo Lj.
AU - Miloradović, M.
PY - 1966
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4685
AB - By means of lead tetra-acetate in refluxing benzene open-chain 1,2-, 1,3-, 1,4- and 1,5-hydroxy-ethers are mainly converted to the corresponding five-membered or six-membered cylic products. Thus, 2-alkoxy-1-ethanols afford 2-substituted 1,3-dioxolanes in 50-53% yield and 4-ethoxy-1-butanol gives 2-ethoxytetrahydrofuran in 52% yield; 3-alkoxy-1-propanols are oxidized to the corresponding 2-substituted 1,3-dioxans in 26-40% yield and 5-ethoxy-1-pentanol cyclizes to 2-ethoxytetrahydropyran in 46% yield. 2-Phenoxyethanol undergoes ring closure to 1,4-benzodioxan in 15% yield.
PB - Elsevier
T2 - Tetrahedron
T1 - The reaction of lead tetra-acetate with some acyclic hydroxy-ethers
VL - 22
IS - 2
SP - 723
EP - 738
DO - 10.1016/0040-4020(66)80043-1
ER -
@article{
author = "Mihailović, Milhailo Lj. and Miloradović, M.",
year = "1966",
abstract = "By means of lead tetra-acetate in refluxing benzene open-chain 1,2-, 1,3-, 1,4- and 1,5-hydroxy-ethers are mainly converted to the corresponding five-membered or six-membered cylic products. Thus, 2-alkoxy-1-ethanols afford 2-substituted 1,3-dioxolanes in 50-53% yield and 4-ethoxy-1-butanol gives 2-ethoxytetrahydrofuran in 52% yield; 3-alkoxy-1-propanols are oxidized to the corresponding 2-substituted 1,3-dioxans in 26-40% yield and 5-ethoxy-1-pentanol cyclizes to 2-ethoxytetrahydropyran in 46% yield. 2-Phenoxyethanol undergoes ring closure to 1,4-benzodioxan in 15% yield.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "The reaction of lead tetra-acetate with some acyclic hydroxy-ethers",
volume = "22",
number = "2",
pages = "723-738",
doi = "10.1016/0040-4020(66)80043-1"
}
Mihailović, M. Lj.,& Miloradović, M.. (1966). The reaction of lead tetra-acetate with some acyclic hydroxy-ethers. in Tetrahedron
Elsevier., 22(2), 723-738.
https://doi.org/10.1016/0040-4020(66)80043-1
Mihailović ML, Miloradović M. The reaction of lead tetra-acetate with some acyclic hydroxy-ethers. in Tetrahedron. 1966;22(2):723-738.
doi:10.1016/0040-4020(66)80043-1 .
Mihailović, Milhailo Lj., Miloradović, M., "The reaction of lead tetra-acetate with some acyclic hydroxy-ethers" in Tetrahedron, 22, no. 2 (1966):723-738,
https://doi.org/10.1016/0040-4020(66)80043-1 . .
