Publication

Fluor-olefine durch Fluormethylenierung von Carbonylverbindungen

1969
Journal Articles

Abstract

Stirred 10.25 g ClO3F in 300 ml MePh at -70 Deg, under N, was treated with 160 ml 0.41M triphenylphosphonium methylide to give 98% [Ph3P+CH2F]ClO3- (I), m. 131-4 Deg (CH2Cl2-AcOH-EtOAc). Satd. 1 equiv. I in Me2CO treated with 1.25 equivs. NaI in Me2CO gave 90% [Ph3P+CH2F]I- (II), m. 169-71 Deg. Stirred 29.5 g II in 450 ml tetrahydrofuran at -78 Deg was treated dropwise with LiBr-contg. LiPh in Et2O to give Ph3P+C-HF which reacted with BzH to give 65% PhCH:CHF (50:50 cis-trans ratio), b65 71-4 Deg. Similarly was prepd. C5H11CH:CHF 45:55 cis-trans ratio b. 100-4 Deg, as well as the following compds. in 50:50 cis-trans ratio: 3-F3CC6H4CH:CHF, 3-ClC6H4CH:CHF, b15 84-7 Deg, and III, m. 138-41 Deg, in 55, 25, 65 and 16% yields, resp. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/93b12867-1e3f-46db-b300-b0e2174eb1ab

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1969
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/93b12867-1e3f-46db-b300-b0e2174eb1ab

About this result

Related concepts (7)

Chlorine

Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

Carbon

Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon makes up about 0.025 percent of Earth's crust. Three isotopes occur naturally, ^12C and ^13C being stable, while ^14C is a radionuclide, decaying with a half-life of about 5,730 years. Carbon is one of the few elements known since antiquity.

Methyllithium

Methyllithium is the simplest organolithium reagent with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive toward water. Oxygen and carbon dioxide are also incompatible with MeLi.