Publication

The selective O-acylation of enolates providing simple entry to O-enesters

Manfred Schlosser
1995
Journal Articles

Abstract

In the presence of catalytic amts. of a fluoride source, O-trimethylsilyl enethers undergo condensation with acyl fluorides to afford O-enesters with high yields. The intermediates and final products are pure (Z) isomers if only one double bond is in conjugation with the oxygen atom whereas (E) isomers prevail if silyl dienethers or trienethers and O-dienesters or O-triensesters are formed. [on SciFinder (R)]

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Manfred Schlosser
1995
Journal Articles

Abstract

Official source

Related concepts (17)

Fluoride

Fluoride (ˈflʊəraɪd,_ˈflɔr-) is an inorganic, monatomic anion of fluorine, with the chemical formula F− (also written [F]−), whose salts are typically white or colorless. Fluoride salts typically have distinctive bitter tastes, and are odorless. Its salts and minerals are important chemical reagents and industrial chemicals, mainly used in the production of hydrogen fluoride for fluorocarbons. Fluoride is classified as a weak base since it only partially associates in solution, but concentrated fluoride is corrosive and can attack the skin.

Fluoride toxicity

Fluoride toxicity is a condition in which there are elevated levels of the fluoride ion in the body. Although fluoride is safe for dental health at low concentrations, sustained consumption of large amounts of soluble fluoride salts is dangerous. Referring to a common salt of fluoride, sodium fluoride (NaF), the lethal dose for most adult humans is estimated at 5 to 10 g (which is equivalent to 32 to 64 mg elemental fluoride/kg body weight). Ingestion of fluoride can produce gastrointestinal discomfort at doses at least 15 to 20 times lower (0.

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.

Related publications (1)

The selective O-acylation of enolates providing simple entry to O-enesters

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Fluorinated analogs of retinoids. Stereocontrolled synthesis employing fluoroisoprenoidal Horner ylides