Publication

a-Deprotonated allyl ethers: conformational mobility and conformational preferences

Manfred Schlosser
1998
Journal Articles

Abstract

Tert-BuLi is best suited to accomplish an H-metal exchange at the a-position of g-alkyl branched allyl ethers. Rapid torsional equilibration occurs at the g-terminus of the deprotonated allyl unit, while the alkoxy group at the a-site has to occupy the exo position in order to minimize steric repulsions. Introduction of an alkoxy group into the terminal position of a g-branched 2-alkenyllithium lowers the barrier to torsional isomerization slightly (by a few kcal/mol). [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/f646ae72-a860-4af2-93bc-26fd99719761

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Manfred Schlosser
1998
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/f646ae72-a860-4af2-93bc-26fd99719761

About this result

Related concepts (27)

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.

Anomeric effect

In organic chemistry, the anomeric effect or Edward-Lemieux effect is a stereoelectronic effect that describes the tendency of heteroatomic substituents adjacent to a heteroatom within a cyclohexane ring to prefer the axial orientation instead of the less hindered equatorial orientation that would be expected from steric considerations. This effect was originally observed in pyranose rings by J. T. Edward in 1955 when studying carbohydrate chemistry. The term anomeric effect was introduced in 1958.

Conformational isomerism

In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted just by rotations about formally single bonds (refer to figure on single bond rotation). While any two arrangements of atoms in a molecule that differ by rotation about single bonds can be referred to as different conformations, conformations that correspond to local minima on the potential energy surface are specifically called conformational isomers or conformers.

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a-Deprotonated allyl ethers: conformational mobility and conformational preferences

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