Publication

Mixed metal bases as promoters of 1,4-eliminations

Manfred Schlosser
1990
Journal Articles

Abstract

When treated with the LIDAKOR mixt., allyl type ethers very readily undergo 1,4-elimination to afford conjugated dienes (E)-H2C:CHCH:CH(CH2)4Me, H2C:C(:CH2)CH2CH2CH:CMe2, H2C:CHCH:CHOMe. In typical cases, the reaction is brought about stereo- and regioselectively, e.g., (E)-H2C:CHCH:CH(CH2)4Me and H2C:C(:CH2)CH2CH2CH:CMe2). Under suitable conditions, lithium dimethylamide or even lithium diisopropylamide adds to the dienes generated in situ thus leading to a variety of new allyl amines Me2C:CHCH2CH2C(CH2NMe2):CHMe, Me2CHCH2CH2CH:CMeCH:CHNMe2, and (Z)-MeCH:CHCH2N(CHMe2)2. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/941c7a88-76df-4ad5-aa4f-8e81ab8a5c72

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Manfred Schlosser
1990
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/941c7a88-76df-4ad5-aa4f-8e81ab8a5c72

About this result

Related concepts (13)

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.

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.

Organoiron chemistry

Organoiron chemistry is the chemistry of iron compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. While iron adopts oxidation states from Fe(−II) through to Fe(VII), Fe(IV) is the highest established oxidation state for organoiron species. Although iron is generally less active in many catalytic applications, it is less expensive and "greener" than other metals.

Related publications (2)

Mixed metal bases as promoters of 1,4-eliminations

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Trifluoromethoxy Substituted Anilines: Metalation as the Key Step for Structural Elaboration

Bridging the final gap in stereocontrolled Wittig reactions: methoxymethoxy-armed allylic phosphorus ylides affording conjugated dienes with high cis selectivity