Journal of Organic Chemistry p. 6528 - 6533 (1994)
Update date:2022-09-26
Topics: Regioselectivity NMR spectroscopy Stereochemistry Deprotonation Cyclization Alkene Workup Intramolecular Reaction Nucleophilic Attack Quenching Ring-closing reaction Gas chromatography (GC) Anionic Cyclization carbanion Organolithium reagent Low-temperature reaction Methoxy group (-OCH?)
Bailey, William F.
Jiang, Xing-Long
The cyclization of (4-methoxy-5-hexenyl)lithium (1), which was prepared by lithium-iodine exchange between 3-methoxy-6-iodo-1-hexene (2) and 1.75 molar equiv of t-BuLi in diethyl ether-n-pentane solution at -78 deg C, has been investigated in variety of solvent systems.The isomeric composition of the cis- and trans-1-methoxy-2-methylcyclopentane produced upon cyclization of 1 followed by quench with MeOH has been found to be dramatically dependent on the solvent system in which the isomerization is conducted.
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