Publication

Regioselective formation of fluorohydrins and their stereoselective conversion to fluoroolefins

Manfred Schlosser
1990
Journal Articles

Abstract

When treated with KOCMe3 in THF, fluorohydrin p-tosylates afford fluoro olefins, e.g., Z- or E-Me(CH2)4CF:CH(CH2)4Me, in high yields. Fluorohydrins are readily and stereoselectively accessible by antiperiplanar addn. of HF to oxiranes. Terminal epoxides give preferentially 2-fluoro-1-alkanols with HF-pyridine mixt. in PhMe, while mainly 1-fluoro-2-alkanols result from reaction with Huenig's hydrofluoride (i.e., the adduct of HF and (Me2CH)2NEt. With 2-hydroxymethyl-substituted oxiranes, 3-fluoro-1,2-alkanediols are obtained predominantly if not exclusively. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/d69c6140-267e-4a35-b7c2-7bae69823cb0

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Manfred Schlosser
1990
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/d69c6140-267e-4a35-b7c2-7bae69823cb0

About this result

Related concepts (15)

Stereoselectivity

In chemistry, stereoselectivity is the property of a chemical reaction in which a single reactant forms an unequal mixture of stereoisomers during a non-stereospecific creation of a new stereocenter or during a non-stereospecific transformation of a pre-existing one. The selectivity arises from differences in steric and electronic effects in the mechanistic pathways leading to the different products. Stereoselectivity can vary in degree but it can never be total since the activation energy difference between the two pathways is finite: both products are at least possible and merely differ in amount.

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