Publication

2-Alkenyl anions and their surprising endo preference. Facile and extreme stereocontrol over carbon-carbon linking reactions with organometallics of the allyl type

Manfred Schlosser
1976
Journal Articles

Abstract

On structural equilibration, butenyl sodium, potassium and cesium strongly favor the cis (endo) configuration over the extended form. The cis-trans ratios vary from 93:7 to 96:4 and 99.9:0.1 in the series Na, K, and Cs; the corresponding value for 2-butene is 23:77. Homologous alkenylmetal compds. exhibit less extreme stereoselectivities, but still follow the same trend. The metal effect on the endo-preference is due to the electropositivity and bulk of the metal as well as intramol. H bonding between the alkyl group attached to the inner side of the allyl moiety with the electron excess accumulated at the other allylic terminus. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/cefae866-da4b-435b-a036-05d9c574b09f

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Manfred Schlosser
1976
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/cefae866-da4b-435b-a036-05d9c574b09f

About this result

Related concepts (31)

Acyl group

In chemistry, an acyl group is a moiety derived by the removal of one or more hydroxyl groups from an oxoacid, including inorganic acids. It contains a double-bonded oxygen atom and an organyl group () or hydrogen in the case of formyl group (). In organic chemistry, the acyl group (IUPAC name alkanoyl if the organyl group is alkyl) is usually derived from a carboxylic acid, in which case it has the formula , where R represents an organyl group or hydrogen.

Alkyl group

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula . Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula .

Organoboron chemistry

Organoboron chemistry or organoborane chemistry is the chemistry of organoboron compounds or organoboranes, which are chemical compounds of boron and carbon that are organic derivatives of borane (BH3), for example trialkyl boranes. . Organoboron compounds are important reagents in organic chemistry enabling many chemical transformations, the most important ones being hydroboration and carboboration. Reactions of organoborates and boranes involve the transfer of a nucleophilic group attached to boron to an electrophilic center either inter- or intramolecularly.

Related publications (4)

2-Alkenyl anions and their surprising endo preference. Facile and extreme stereocontrol over carbon-carbon linking reactions with organometallics of the allyl type

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