Publication

Selective syntheses with organometallics. VI. Capricious stereoselectivities of alkenylpotassium formation under kinetic and thermodynamic control. Oxygen-triggered configurational equilibration of an allyl type organometallic compound

Manfred Schlosser
1977
Journal Articles

Abstract

Metalation at the allylic site (Me group) of (Z)-RCH:CHMe (R = alkyl) is more rapid than with the E-isomers regardless of the configuration in which the resultant organometallic is more thermodn. stable. Thus, (Z)-Me3CCH:CHCH2K is formed 15 times faster than its E-isomer, although the latter is thermodn. favored. Isomerization of the allylpotassium compds. in THF is very slow, but may be catalyzed by trace impurities, e.g., O. [on SciFinder (R)]

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Manfred Schlosser
1977
Journal Articles

Abstract

Official source

Related concepts (18)

Isomer

In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism refers to the existence or possibility of isomers. Isomers do not necessarily share similar chemical or physical properties. Two main forms of isomerism are structural or constitutional isomerism, in which bonds between the atoms differ; and stereoisomerism or spatial isomerism, in which the bonds are the same but the relative positions of the atoms differ.

Cis–trans isomerism

Cis–trans isomerism, also known as geometric isomerism or configurational isomerism, is a term used in chemistry that concerns the spatial arrangement of atoms within molecules. The prefixes "cis" and "trans" are from Latin: "this side of" and "the other side of", respectively. In the context of chemistry, cis indicates that the functional groups (substituents) are on the same side of some plane, while trans conveys that they are on opposing (transverse) sides.

Stereoisomerism

In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

Related publications (10)

Selective syntheses with organometallics. VI. Capricious stereoselectivities of alkenylpotassium formation under kinetic and thermodynamic control. Oxygen-triggered configurational equilibration of an allyl type organometallic compound

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