The lead tetraacetate oxidation of Δ6-unsaturated tertiary alcohols. Eight-membered cyclic ether formation
Апстракт
In the lead tetraacetate oxidation of the unsaturated tertiary cyclic alcohols 1a and 1b, and the acyclic alcohol 15a, all possessing a Δ6-olefinic bond (with respect to the hydroxyl group), the α-acetoxylated eight-membered cyclic ethers 6a, 6b and 16a, respectively, were obtained. With these substrates lead tetraaeetate reacts at the double bond and, if at all, only by weak association with the hydroxyl group, so that fragmentation products derived from alkoxy radical intermediates (such as 2) were not formed. The mechanism of this cyclisation reaction is discussed. © 1989, Springer. All rights reserved.
Извор:
Research on Chemical Intermediates, 1989, 11, 3, 257-270Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Ceković, ž. AU - Saičić, Radomir AU - Mihailović, M.L. PY - 1989 UR - https://cherry.chem.bg.ac.rs/handle/123456789/95 AB - In the lead tetraacetate oxidation of the unsaturated tertiary cyclic alcohols 1a and 1b, and the acyclic alcohol 15a, all possessing a Δ6-olefinic bond (with respect to the hydroxyl group), the α-acetoxylated eight-membered cyclic ethers 6a, 6b and 16a, respectively, were obtained. With these substrates lead tetraaeetate reacts at the double bond and, if at all, only by weak association with the hydroxyl group, so that fragmentation products derived from alkoxy radical intermediates (such as 2) were not formed. The mechanism of this cyclisation reaction is discussed. © 1989, Springer. All rights reserved. T2 - Research on Chemical Intermediates T1 - The lead tetraacetate oxidation of Δ6-unsaturated tertiary alcohols. Eight-membered cyclic ether formation VL - 11 IS - 3 SP - 257 EP - 270 DO - 10.1163/156856789X00375 ER -
@article{ author = "Ceković, ž. and Saičić, Radomir and Mihailović, M.L.", year = "1989", abstract = "In the lead tetraacetate oxidation of the unsaturated tertiary cyclic alcohols 1a and 1b, and the acyclic alcohol 15a, all possessing a Δ6-olefinic bond (with respect to the hydroxyl group), the α-acetoxylated eight-membered cyclic ethers 6a, 6b and 16a, respectively, were obtained. With these substrates lead tetraaeetate reacts at the double bond and, if at all, only by weak association with the hydroxyl group, so that fragmentation products derived from alkoxy radical intermediates (such as 2) were not formed. The mechanism of this cyclisation reaction is discussed. © 1989, Springer. All rights reserved.", journal = "Research on Chemical Intermediates", title = "The lead tetraacetate oxidation of Δ6-unsaturated tertiary alcohols. Eight-membered cyclic ether formation", volume = "11", number = "3", pages = "257-270", doi = "10.1163/156856789X00375" }
Ceković, ž., Saičić, R.,& Mihailović, M.L.. (1989). The lead tetraacetate oxidation of Δ6-unsaturated tertiary alcohols. Eight-membered cyclic ether formation. in Research on Chemical Intermediates, 11(3), 257-270. https://doi.org/10.1163/156856789X00375
Ceković Ž, Saičić R, Mihailović M. The lead tetraacetate oxidation of Δ6-unsaturated tertiary alcohols. Eight-membered cyclic ether formation. in Research on Chemical Intermediates. 1989;11(3):257-270. doi:10.1163/156856789X00375 .
Ceković, ž., Saičić, Radomir, Mihailović, M.L., "The lead tetraacetate oxidation of Δ6-unsaturated tertiary alcohols. Eight-membered cyclic ether formation" in Research on Chemical Intermediates, 11, no. 3 (1989):257-270, https://doi.org/10.1163/156856789X00375 . .