Publication

Base-promoted elimination of hydrogen fluoride from alkyl fluorides: reactivity and stereochemistry

Manfred Schlosser
1988
Journal Articles

Abstract

The alcoholate-promoted dehydrohalogenation of 5-nonyl fluoride and cyclododecyl fluoride, typical straight-chain and, resp., medium-size cyclic substrates, leads to cis- and trans-alkenes in an approx. ratio of 1:3. With bulky bases such as lithium diisopropylamide the trans isomer is obtained almost exclusively. In general, the elimination of hydrogen fluoride proceeds very slowly. Increase of the base strength has only a moderate effect on the rates. Electrophilic assistance as provided by lithium cations in media of low polarity can, however, considerably accelerate the reaction. Cyclododecyl fluoride cannot be prepd. from cyclododecanol. It is, however, readily accessible by bromofluorination of cyclodecene and subsequent redn. of the adduct with stannane. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/982aa1b0-af46-4dc0-8b82-c54c7e96021e

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Manfred Schlosser
1988
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/982aa1b0-af46-4dc0-8b82-c54c7e96021e

About this result

Related concepts (31)

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.

Hydrogen fluoride

Hydrogen fluoride (fluorane) is an inorganic compound with chemical formula . It is a very poisonous, colorless gas or liquid that dissolves in water to yield an aqueous solution termed hydrofluoric acid. It is the principal industrial source of fluorine, often in the form of hydrofluoric acid, and is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers, e.g. polytetrafluoroethylene (PTFE). HF is also widely used in the petrochemical industry as a component of superacids.

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.

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Base-promoted elimination of hydrogen fluoride from alkyl fluorides: reactivity and stereochemistry

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