Silver tetrafluoroborate

In the course of my studies I also introduced silver tetrafluoroborate, AgBp4, as a metathetic cation forming agent suitable for forming varied ionic (electrophilic) reagents. 

The silver fluorocomplexes, ie, silver hexafluoroantimonate [26042-64-8], AgSbF silver hexafluorophosphate [26042-63-7], AgPF silver tetrafluoroborate [14104-20-2], AgBF and other salts such as silver trifluoromethane sulfonate [2923-28-6], CF SO Ag, and silver trifluoroacetate [2966-50-9], CF COOAg, play an important role in the synthesis of organic compounds and have gained potential industrial importance. 

Silver Tetrafluoroborate. Silver tetrafluoroborate [14104-20-2], AgBF, is formed from silver borate and sodium borofluoride or bromine trifluoride. It is soluble in organic solvents. 

The corresponding tetrafluoroborate is obtained when silver tetrafluoroborate is used. 

PhenyI-3,3-dichIoro-l-azetine (222) forms a 2 1 complex with silver tetrafluoroborate and 1 1 complexes with silver trifluoromethanesulfonate and with boron trifluoride. The dibromo analogue of (222) affords a similar 2 1 complex with silver tetrafluoroborate (79CB3914). 

This topic has been reviewed [2, pp 94, 100-111, 130-134] All of the standard approaches to the synthesis of a compound like methyl 2-fluorostearate from methyl 2-bromostearate result mall yield of the 2-fluoro ester and the unsaturated esters. Although silver fluoride is not a new reagent, its use moist in wet acetonitrile to convert methyl 2-bromostearate to its fluoro ester is a departure from the traditional set of anhydrous conditions (Procedure 6, p 194) [71] In contrast, silver tetrafluoroborate converts a-chloroketones to their respective fluoroketones under anhydrous conditions. The displacement of less activated halogen groups by silver tetrafluoroborate to form their respective fluorides is novel Although silver tetrafluoroborate could not be used to convert an aliphatic terminal dichloromethyl or trichloromethyl group to its corresponding fluoro derivative, it is an effective fluorine source in other situations [72] (Table 8)... 

Table 8. Halogen Exchange with Silver Tetrafluoroborate [72]...

The rhodium and iridium complexes of dibenzothiophene (L) reveal an interesting case of linkage isomerism (91IC5046). Thus, the ti S) coordinated species [MCp LCb] on thermolysis with silver tetrafluoroborate afford the Ti -coordinated dicationic species. 

Complex 105 enters the pyrazoleAriphenylphosphine ligand substitution reaction with PPha to give 108 (910M3123). Further reaction with triphenylphosphine and silver tetrafluoroborate gives the heterodinuclear complex 109 (94IC2196). 

The N-coordinated compound [AuCljL] (L= l-ethyl-2-phenylimidazole) with silver tetrafluoroborate gives the cycloaurated species 102, which on further reaction with triphenylphosphine and sodium tetrafluoroborate or ammonium hexafluorophosphate forms the cationic complexes 103 (X = BF., PF,) (00JCS(D)271). 

Chiral alcohols have also been used in an asymmetric synthesis of sulphoxides based on halogenation of sulphides. Johnson and coworkers have found319 that the reaction of benzyl p-tolyl sulphide with JV-chlorobenzotriazole (NCBT) followed by addition of (—) menthol and silver tetrafluoroborate afforded diastereoisomeric menthoxysulphonium salts 267 which, upon recrystallization and hydrolysis, gave benzyl p-tolyl sulphoxide with 87% optical purity (equation 145). More recently, Oae and coworkers reported320 that optically active diaryl sulphoxides (e.e. up to 20%) were formed either by hydrolysis or thermolysis of the corresponding diaryl menthoxysulphonium salts prepared in situ from diaryl sulphides using ( —) menthol and t-butyl hypochlorite. 

The interaction between nitromethane, the etherate of boron trifluoride and silver oxide gives rise to an extremely dangerous reaction. However, it is difficult to interpret it. Can it be explained by the unstable property of silver tetrafluoroborate or the destabilising effect of boron trifluoride on nitromethane ... 

Boron trifluoride etherate, Nitromethane See Silver tetrafluoroborate... 

Bis[Ar,Ar -di(2-pyridyl)- and -di(2-pyridyl-methyl)-imidazol-2-ylidene]aurate(i) tetrafluoroborates have been prepared from the analogous silver complexes on reaction with (tht)AuCl and their structures determined. The configuration of the cations with sterically well-protected two-coordinate gold centers shows no anomalies. However, fascinating structures are found for the adducts with silver tetrafluoroborate obtained as acetonitrile... 

Silver tetrafluoroborate, 22 674, 23 715 Silver thiocyanate, 22 674 Silver thiosulfate, 22 674, 675 in floristry, 22 659, 669 wastewater treatment plants and, 22 683... 

Silver tetrafluoroborate in ether or toluene has also been used for the synthesis of glycosyl fluorides. Peracetylated 2-chloro-2-deoxy-D-gluco- and -mannopyranosyl fluorides have been prepared by treatment of the corresponding chlorides with the aforementioned reagent.50,51 Products of kinetic control were obtained when diethyl ether was used as the solvent, whereas products of thermodynamic control were obtained when toluene was used instead. Peracetylated... 

Ultrasound irradiation of mixtures of amines RNH2 (R = PI1CH2, Ph or Ar) and methyl pyruvate results in the 3-pyrrolin-2-ones 322377. The silver tetrafluoroborate-catalysed cyclization of the allenic amines 323 leads either to a pyrroline 324 or tetrahydropyridine 325, depending on the structure of the amine. The former is formed from 323 (R = H), the latter from 323 (R = Me)378. 

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