Publication

Syntheses of organofluorine compounds. VIII. Solvolytic ring-opening of alkoxychlorofluorocyclopropanes: a ready access to fluorinated a,b-unsaturated aldehydes and ketones

Manfred Schlosser
1977
Journal Articles

Abstract

1-Chloro-1-fluorocyclopropanes [I; R, R1, R2, R3 = H, OMe, Me, Me; Me, OMe, H, H; H, OMe, Me, Me2CH(CH2)3; H, OMe, Me, Me2C:CHCH2CH2; Me, Me, H, MeOCH:CMeCH2CH2; H, OEt, H, Me] were easily prepd. by cycloaddn. of ClFC: to alkenyl ethers in a 2-phase system. I were solvolyzed by heating in an aq. solvent mixt. to give 2-fluoro-2-alkenals, which were readily reduced by LiAlH4 to the corresponding 2-fluoro-2-alkenols. [on SciFinder (R)]

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Manfred Schlosser
1977
Journal Articles

Abstract

Official source

Related concepts (32)

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.

Carbonyl reduction

In organic chemistry, carbonyl reduction is the organic reduction of any carbonyl group by a reducing agent. Typical carbonyl compounds are ketones, aldehydes, carboxylic acids, esters, and acid halides. Carboxylic acids, esters, and acid halides can be reduced to either aldehydes or a step further to primary alcohols, depending on the strength of the reducing agent; aldehydes and ketones can be reduced respectively to primary and secondary alcohols. In deoxygenation, the alcohol can be further reduced and removed altogether.

Ketone

In organic chemistry, a ketone ˈkiːtoʊn is a functional group with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.

Related publications (19)

Syntheses of organofluorine compounds. VIII. Solvolytic ring-opening of alkoxychlorofluorocyclopropanes: a ready access to fluorinated a,b-unsaturated aldehydes and ketones

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