Publication

A simple method for the displacement of bromine by fluorine at tertiary, benzylic or non-classical secondary sites

Manfred Schlosser
2002
Journal Articles

Abstract

Using in situ generated iodine fluoride as the reagent, bromine can be replaced by fluorine at carbocation-sustaining sites. Iodine fluoride or, being its operational equiv., the mixt. of N-iodosuccinimide and triethylamine tris(hydrogen fluoride) reacts with tertiary and benzylic bromoalkanes to afford the resp. fluoroalkanes in moderate-to-excellent yields. In contrast, primary bromoalkanes are virtually inert under identical conditions. Secondary bromoalkanes do not react either unless the heterolytically generated cationic intermediates benefit from non-classical resonance stabilization. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/fed0e427-c2a4-4cbf-a9d4-1d4d93a3a43a

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Manfred Schlosser
2002
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/fed0e427-c2a4-4cbf-a9d4-1d4d93a3a43a

About this result

Related concepts (26)

Haloalkane

The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins.

Iodine

Iodine is a chemical element with the symbol I and atomic number 53. The heaviest of the stable halogens, it exists as a semi-lustrous, non-metallic solid at standard conditions that melts to form a deep violet liquid at , and boils to a violet gas at . The element was discovered by the French chemist Bernard Courtois in 1811 and was named two years later by Joseph Louis Gay-Lussac, after the Ancient Greek Ιώδης 'violet-coloured'. Iodine occurs in many oxidation states, including iodide (I−), iodate (IO3-), and the various periodate anions.

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.