Publication

Syntheses of organofluorine compounds. VII. Structurally biased 2-fluoroallyl cations as generated (or not generated) in cyclopropane ring-opening reactions

Manfred Schlosser
1977
Journal Articles

Abstract

The Ag ion-catalyzed ring-opening of a 1:4 mixt. of syn- and anti-cyclopropanes I and II gave the expected mixt. of CH2:CFC(OH)MeCMe3 and (Z)-MeC(CMe3):CFCH2OH in 56 and 19% yield, resp. Under similar conditions spiro analog. III underwent Wagner-Meerwein rearrangement to give bicycloheptane IV. Mechanism of the reactions are discussed. [on SciFinder (R)]

Official source

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Manfred Schlosser
1977
Journal Articles

Abstract

Official source

Related concepts (18)

Organofluorine chemistry

Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity.

Organobromine chemistry

Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.

Carbon–fluorine bond

The carbon–fluorine bond is a polar covalent bond between carbon and fluorine that is a component of all organofluorine compounds. It is one of the strongest single bonds in chemistry (after the B–F single bond, Si–F single bond, and H–F single bond), and relatively short, due to its partial ionic character. The bond also strengthens and shortens as more fluorines are added to the same carbon on a chemical compound. As such, fluoroalkanes like tetrafluoromethane (carbon tetrafluoride) are some of the most unreactive organic compounds.