Publication

Hydrogen fluoride abstraction from vicinal difluoroalkanes: reaction conditions and syn/anti-stereoselectivity

Manfred Schlosser
1988
Journal Articles

Abstract

vic-Difluoroalkanes are as inert as monofluoroalkanes toward NaOMe in MeOH. Stronger bases, however, can perform dehydrofluorinations relatively smoothly. KOCMe3 in THF at 75 Deg acts exclusively by an antiperiplanar process: meso- and dl-6,7-difluorododecane are converted to (E)- and (Z)-6-fluoro-6-dodecene, resp. Lithium diisopropylamide was an extremely powerful eliminating reagent when employed in hexane, while its reactivity is considerably diminished in di-Et ether and has almost completely vanished in THF. This solvent effect together with the loss of stereoselectivity points at an electrophilic assistance as the key event in lithium amide-induced dehydrofluorinations. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/ab6594f6-6d08-4d9b-95c5-6a638696d25e

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Manfred Schlosser
1988
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/ab6594f6-6d08-4d9b-95c5-6a638696d25e

About this result

Related concepts (18)

Lewis acids and bases

A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons.

Base (chemistry)

In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century. In 1884, Svante Arrhenius proposed that a base is a substance which dissociates in aqueous solution to form hydroxide ions OH−. These ions can react with hydrogen ions (H+ according to Arrhenius) from the dissociation of acids to form water in an acid–base reaction.

Chiral auxiliary

In stereochemistry, a chiral auxiliary is a stereogenic group or unit that is temporarily incorporated into an organic compound in order to control the stereochemical outcome of the synthesis. The chirality present in the auxiliary can bias the stereoselectivity of one or more subsequent reactions. The auxiliary can then be typically recovered for future use. Most biological molecules and pharmaceutical targets exist as one of two possible enantiomers; consequently, chemical syntheses of natural products and pharmaceutical agents are frequently designed to obtain the target in enantiomerically pure form.

Related publications (2)

Hydrogen fluoride abstraction from vicinal difluoroalkanes: reaction conditions and syn/anti-stereoselectivity

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