Publication

Vicinal bromofluoroalkanes: their regioselective formation and their conversion to fluoro olefins

Manfred Schlosser
1990
Journal Articles

Abstract

Reaction of alkenes with N-bromosuccinimide and Et3N.3HF produces vic-bromofluoroalkanes in high yields. As long as the addn. to the C:C bond is sterically unhindered, Br and F get attached with very high regioselectivity, the latter occupying the more substituted, carbocation-stabilizing position. 2-Fluoro-1-alkenes give 1-bromo-2,2-difluoroalkanes. The Br may be removed by base-promoted dehydrofluorination to afford fluoro olefins, or by redn. with Bu3SnH, leading to mono- or difluoroalkanes. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/8364856e-4b1d-49c5-ab54-c2f05f8a29f3

About this result

This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.

Graph Chat

Chat with Graph Search

Ask any question about EPFL courses, lectures, exercises, research, news, etc. or try the example questions below.

DISCLAIMER: The Graph Chatbot is not programmed to provide explicit or categorical answers to your questions. Rather, it transforms your questions into API requests that are distributed across the various IT services officially administered by EPFL. Its purpose is solely to collect and recommend relevant references to content that you can explore to help you answer your questions.

Manfred Schlosser
1990
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/8364856e-4b1d-49c5-ab54-c2f05f8a29f3

About this result

Related concepts (14)

Alkene

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc.

Alkyne trimerisation

An alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units () react to form a benzene ring. The reaction requires a metal catalyst. The process is of historic interest as well as being applicable to organic synthesis. Being a cycloaddition reaction, it has high atom economy. Many variations have been developed, including cyclisation of mixtures of alkynes and alkenes as well as alkynes and nitriles. Trimerisation of acetylene to benzene is highly exergonic, proceeding with a free energy change of 142 kcal/mol at room temperature.

Dehydrohalogenation

In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Traditionally, alkyl halides are substrates for dehydrohalogenations. The alkyl halide must be able to form an alkene, thus halides having no C–H bond on an adjacent carbon are not suitable substrates. Aryl halides are also unsuitable. Upon treatment with strong base, chlorobenzene dehydrohalogenates to give phenol via a benzyne intermediate.