S. Stavber, M. Zupan
Jul 1, 1992
Citations
0
Influential Citations
14
Citations
Journal
Tetrahedron
Abstract
Abstract CsSO4F 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, 4-tert-butylphenol, benzaldehyde, and octanal, thus forming fluorotriphenylmethane, fluorotriphenylsilane, 2-fluoro-4-tert-butylphenol, benzoyl fluoride, or octanoyl fluoride in high yields. Substitution reaction was accompanied by fluoroaddition process in the case of 2-fluoro-4-tert-butylphenol, where 2,2-difluoro-4-tert-butylcyclohexadienon-4,6 was isolated. CsSO4F easily oxidised secondary alcohols to ketones, and 1,2-dihydroxy-4-tert-butylbenzene to quinone derivate. Oxygenation process was observed in the case of triphenylphosphine, and dibenzotiophene, while ethyl iodide was transformed to ethyliodo(III) difluoride. Solvent plays an important role in these reactions, being successfully performed in CH3CN, and completely inhibited in CH2Cl2, while different shapes of the effect on fluorination of various organic molecules were observed by altering solvent nature by successive mixing of CH3CN with CH2Cl2.