Publication

Konfigurativ einheitliche Folgeprodukte aus Alkenylkalium-Zwischenstufen

Manfred Schlosser
1974
Journal Articles

Abstract

Me groups adjacent to an olefinic double bond were metalated by KOCMe3 and BuLi without cis-trans isomerization. Thus, (E)-MeCH:-CHMe was metalated to give (E)-MeCH:CHCH2K (I) which reacted with ethylene oxide to give 41% (E)-MeCH:CH(CH2)3OH. If I was allowed to equilibrate, the Z-isomer predominated (>99:1). Longer-chain olefins were metalated more slowly, with side reactions taking place. Thus, metalation of BuCH:CMe2 with EtCHMeBu and KOCMe3, followed by reaction with MeI gave 45% (Z)-BuCH:CMeEt, 9% BuCHMeCMe:CH2, and 19% Me(CH2)4CEt:CH2. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/e1073187-29d1-4047-885b-14854a8332b6

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Manfred Schlosser
1974
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/e1073187-29d1-4047-885b-14854a8332b6

About this result

Related concepts (24)

Alkene

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc.

Ethylene oxide

Ethylene oxide is an organic compound with the formula . It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.

Ethylene

Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon double bonds). Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016) exceeds that of any other organic compound. Much of this production goes toward polyethylene, a widely used plastic containing polymer chains of ethylene units in various chain lengths.

Related publications (3)

Konfigurativ einheitliche Folgeprodukte aus Alkenylkalium-Zwischenstufen

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Ynimines as versatile precursors to 2-imido- and 2-amido-1,3-dienes for stereodivergent diels–alder reactions

Electrochemical promotion of an IrO2 catalyst for the gas phase oxidation of ethylene

Increasing the selectivity in manufacturing ethylene oxide