Oxofluorination reaction

A novel reaction of perchloryl fluoride with aromatic substrates was discovered by Neeman and Osawa, the oxofluorination reaction. These authors found that reaction of indene with perchloryl fluoride in dioxane-water yields five products, the major product being, 2-fluoroindanone. When applied to 6-dehydroestradiol diacetate (24) there is obtained as the major product the 7a-fluoro-6-ketone (25). Borohydride reduction of the... 

For the oxofluorination reaction, a transition state (29) has been proposed which possesses features of a benzylic carbonium ion. This leads by... 

Compounds having a cyclic double bond conjugated with an aromatic ring are capable of reacting with FCIO3 to give a-fluoroketones. This type of reaction was named oxofluorination and in it FCIO3 acts as a 2-center electrophile as shown for indene (207) ... 

A reaction in which perchloryl fluoride functions as an ambident electrophile, somewhat analogous to Neeman s oxofluorination, was discovered by Kende and MacGregor on passing FCIOj into a suspension of sodium 2,6-dimethylphenoxide in pentane or toluene at 0°. Workup and chromatography gave 2,6-dimethylphenol, 2,6-dimethylbenzoquinone, 2,2, 6,6 -tetramethyl-4,4 -diphenoquinone and, in about 20% yield, a new compound characterized as the dimer (3) of 6-fluoro-2,6-dimethyl-... 

Oxofluorination. This is the name given hy Neeman to a new electrophilic nmhidcnt reaction of perchloryl fluoride with olefins of the type of indene (1). A solution of indene in aqueous dioxane is kept saturated with FCIO at room... 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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