TY  - JOUR
AU  - Mihailovíć, Mihailo Lj.
AU  - Vukićević, Rastko
AU  - Konstantinović, Stanimir
AU  - Milosavljević, Slobodan
AU  - Schroth, Gerhard
PY  - 1992
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4740
AB  - Reactions of some primary and secondary Δ4‐, Δ5‐ and Δ6‐alkenols with thallium triacetate (TTA) in benzene, acetic acid and chloroform as solvent have been investigated. When terminally unsubstituted Δ4‐alkenols, such as 4‐penten‐1‐ol (5a) and 5‐hexen‐2‐ol (5b), are treated with TTA in benzene, β‐acetoxylated tetrahydrofurans 8a and 8b are obtained. However, when the reaction is carried in acetic acid the products are both regioisomers, i.e. five‐ and six‐membered cyclic ethers (8a, 8b, 7a and 7b). 4‐Methyl‐4‐penten‐1‐ol (5c) is converted in benzene into a mixture of products (8c and 7c) in which the tetrahydropyran derivative 7c is predominant, and in acetic acid it is the sole cyclization product. Terminally dialkylated alkenols, such as 5‐methyl‐4‐hexen‐1‐ol (1b) and 6‐methyl‐5‐hepten‐2‐ol (1c), are converted into β‐acetoxylated (4b and 4c) and unsaturated cyclic ethers (9a and 9b), in both cases of the tetrahydrofuran type. 5‐Hexen‐1‐ol (10) and 6‐hepten‐1‐ol (11) cyclize to the corresponding six‐ (13) and seven‐membered cyclic ether (14), respectively. Organothallium intermediates have been isolated and identified in the cases of alcohols 5a, 5c and 10, proving that the TTA addition to the double bond has originally obeyed the Markovnikov rule.
PB  - Weinheim : Wiley-VCH Verlag GmbH & Co.
T2  - Liebigs Annalen der Chemie
T1  - Intramolecular Cyclization of Some Unsaturated Alcohols by Means of Thallium Triacetate
VL  - 1992
IS  - 4
SP  - 305
EP  - 309
DO  - 10.1002/jlac.199219920156
ER  - 

@article{
author = "Mihailovíć, Mihailo Lj. and Vukićević, Rastko and Konstantinović, Stanimir and Milosavljević, Slobodan and Schroth, Gerhard",
year = "1992",
abstract = "Reactions of some primary and secondary Δ4‐, Δ5‐ and Δ6‐alkenols with thallium triacetate (TTA) in benzene, acetic acid and chloroform as solvent have been investigated. When terminally unsubstituted Δ4‐alkenols, such as 4‐penten‐1‐ol (5a) and 5‐hexen‐2‐ol (5b), are treated with TTA in benzene, β‐acetoxylated tetrahydrofurans 8a and 8b are obtained. However, when the reaction is carried in acetic acid the products are both regioisomers, i.e. five‐ and six‐membered cyclic ethers (8a, 8b, 7a and 7b). 4‐Methyl‐4‐penten‐1‐ol (5c) is converted in benzene into a mixture of products (8c and 7c) in which the tetrahydropyran derivative 7c is predominant, and in acetic acid it is the sole cyclization product. Terminally dialkylated alkenols, such as 5‐methyl‐4‐hexen‐1‐ol (1b) and 6‐methyl‐5‐hepten‐2‐ol (1c), are converted into β‐acetoxylated (4b and 4c) and unsaturated cyclic ethers (9a and 9b), in both cases of the tetrahydrofuran type. 5‐Hexen‐1‐ol (10) and 6‐hepten‐1‐ol (11) cyclize to the corresponding six‐ (13) and seven‐membered cyclic ether (14), respectively. Organothallium intermediates have been isolated and identified in the cases of alcohols 5a, 5c and 10, proving that the TTA addition to the double bond has originally obeyed the Markovnikov rule.",
publisher = "Weinheim : Wiley-VCH Verlag GmbH & Co.",
journal = "Liebigs Annalen der Chemie",
title = "Intramolecular Cyclization of Some Unsaturated Alcohols by Means of Thallium Triacetate",
volume = "1992",
number = "4",
pages = "305-309",
doi = "10.1002/jlac.199219920156"
}

Mihailovíć, M. Lj., Vukićević, R., Konstantinović, S., Milosavljević, S.,& Schroth, G.. (1992). Intramolecular Cyclization of Some Unsaturated Alcohols by Means of Thallium Triacetate. in Liebigs Annalen der Chemie
Weinheim : Wiley-VCH Verlag GmbH & Co.., 1992(4), 305-309.
https://doi.org/10.1002/jlac.199219920156

Mihailovíć ML, Vukićević R, Konstantinović S, Milosavljević S, Schroth G. Intramolecular Cyclization of Some Unsaturated Alcohols by Means of Thallium Triacetate. in Liebigs Annalen der Chemie. 1992;1992(4):305-309.
doi:10.1002/jlac.199219920156 .

Mihailovíć, Mihailo Lj., Vukićević, Rastko, Konstantinović, Stanimir, Milosavljević, Slobodan, Schroth, Gerhard, "Intramolecular Cyclization of Some Unsaturated Alcohols by Means of Thallium Triacetate" in Liebigs Annalen der Chemie, 1992, no. 4 (1992):305-309,
https://doi.org/10.1002/jlac.199219920156 . .