Vinyltin compounds fluorination

Table 9. Fluorination of Vinyltin Compounds with F-Teda BF4 (6) in Acetonitrile88...

One of the most convenient synthetic routes for the preparation of vinyl fluorides 2 is by treatment of the corresponding vinyltin compounds 1 with electrophilic fluorinating reagents. This procedure is also used for the preparation of aryl fluorides, since it is well-established that fluorination with electrophilic reagents is facilitated by ipso substitution of a suitable, usually weakly bonded, metal function. In the case of aryl fluorides, the reaction is also carried out using elemental fluorine as the fluorinating agent. ... 

Xenon difluoride (XeF ) is the electrophilic fluorinating reagent whose reactions with vinyltin compounds have been studied most exhaustively. " A series of vinyl fluorides prepared according to this procedure is listed in Table 1. 

Fluorination of Vinyltin Compounds with Xenon Difluoride (XcFj) General Procedure ... 

Xenon difluoride is a better fluorinaling reagent for vinyltin compounds than cesium fluoroxysulfate (compare entry 1 in Tables 1 and 2). Besides this, cesium fluoroxysulfate (which can be prepared from elemental fluorine and cesium sulfate) is known to be shock sensitive and to undergo detonation upon hcaling. However, cesium fluoroxysulfate is the alternative choiee in the ease of some vinyltin compounds, such as 2- and 3-(trimethylstannyl)indolcs (Table 2, entries 5 7), whose reactions with xenon difluoride are not effective. 

Fluorination of Vinyltin Compounds with t-(Chloromethyl)-4-fluoro-l,4 iazoniabicyclo 2.2.2]octane Bis(tct-rafluoroborate) (F-Teda BFj ) General Procedure ... 

Fluorination of Vinyltin Compounds with Cesium Fluoroxysulfate General Procedure 10... 

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See also in sourсe #XX -- [ , ]

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