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The effect of heteroatoms on the reactions of organic molecules with caesium fluoroxysulphate

✍ Scribed by Stojan Stavber; Marko Zupan


Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
634 KB
Volume
48
Category
Article
ISSN
0040-4020

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✦ Synopsis


CsSOeF reacted at room temperature, or at 35'C in acetonitrile with various heteroatom-containing organic molecules, and three types of transformations have been observed. Fluoro substitution process took place with triphenylmethane, triphenylsilane, triphenylchlorosilane, Ctertbutylphenol, benzaldehyde, and o&anal, thus forming fluorotriphenylmethane, fluorotriphenylsilane, 2-fluoro-4-tertbutylphenol, benzoyl fluoride, or octanoyl fluoride in high yields. Substitution reaction was accompanied by fluoroaddition process in the case of 2-fluoro-4tert-butylphenol, where 2,2-difluoro-4-tert-butylcyclohexadienon-4,6 was isolated. CsSO,F easily oxidised secondary alcohols to ketones, and 1,2-dihydroxy-4-tertbutylbenzene to quinone derivate. Oxygenation process was observed in the case of triphenylphosphine, and dibenzotiophene, while ethyl iodide was transformed to ethyliodo(II1) difluoride. Solvent plays an important role in these reactions, being successfully performed in CH,CN, and completely inhibited in CH,CI,, while different shapes of the effect on fluorination of various organic molecules were observed by altering solvent nature by successive mixing of CH,CN with CH,Cl,.


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