Publication

Hydroxyäthylallene und andere Folgeprodukte aus Dihydrofuran-Derivaten

Manfred Schlosser
1975
Journal Articles

Abstract

Upon treatment with organolithium compds., 2-alkyl-4,5-dihydrofurans underwent ring opening through b-elimination to give the corresponding 3,4-dien-1-ol. 3-Chloro-2-methyl-4,5-dihydrofuran gave 3-chloro-3,4-dien-1-ol as a reaction intermediate, but it could not be isolated. Its formation was slow compared to subsequent replacement of halogen by the org. moiety of the alkyllithium reagent. Under certain reaction conditions, the 3,4-pentadien-1-ol which formed isomerized to terminal acetylenes, which, as well as their allene precursors, could be converted with Na-NH3 into 4-penten-1-ol or 3-penten-1-ol derivs. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/075e0ea0-22d6-413d-b4d6-a86f94b472b5

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Manfred Schlosser
1975
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/075e0ea0-22d6-413d-b4d6-a86f94b472b5

About this result

Related concepts (19)

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Alkyne

Acetylene Propyne 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula . Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.

Isomerization

In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomerization. When the isomerization occurs intramolecularly it may be called a rearrangement reaction. When the activation energy for the isomerization reaction is sufficiently small, both isomers will exist in a temperature-dependent equilibrium with each other.

Related publications (8)

Hydroxyäthylallene und andere Folgeprodukte aus Dihydrofuran-Derivaten

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