5492-84-2

Upstream product

• 344-04-7 bromopentafluorobenzene 
• 10386-84-2 4,4'-dibromo-2,3,5,6,2',3',5',6'-octafluoro-1,1'-biphenyl 
• 1038-65-9 4-bromo-2,2',3,3',4',5,5',6,6'-nonafluoro-1,1'-biphenyl 

Relevant academic research and scientific papers

Halophilic reactions of pentafluorohalobenzenes with transition-metal carbonyl anions

In the present work we widen the scope of the halophilic mechanism of nucleophilic aromatic substitution, which we found earlier for the reaction of pentafluorochlorobenzene with [CpFe(CO)2]- anion, to reactions of pentafluorohalobenzenes (Hal=Cl, Br, I) with various metal carbonyl anions [Re(CO)5]-, [Mn(CO)5]- and [CpFe(CO)2]-. Nucleophilic aromatic substitution with the [CpFe(CO)2]- anion yields C6F5Fe(CO)2Cp, while with [Re(CO)5]- and [Mn(CO)5]- anions the halo(acyl)metallates cis-[C6F5(CO)M(CO)4Hal]Na (M=Mn, Re) are obtained.

Halophilic mechanism of nucleophilic aromatic substitution in pentafluorohalobenzenes with anions of transition metal carbonyls

Reactions were stadied between anions of transition metal carbonyls [carbonylates CpFe(CO)-2, Re(CO)-5, and Mn(CO)-5 with pentafluorohalobenzenes C6F5Hlg, where Hlg = Cl, Br, I. In all reactions operates the halophilic mechanism of nucleophilic substitution with exchange of metal for halogen between haloarene and carbonylate as the key stage. The formation of anionic haloacylic complexes of rhenium and manganese carbonyls, cis-[C6F5(CO)M(CO)4Hlg]-M1+ (M = Re, M1 = Na; M = Mn, M1 = K) in reaction of C6F5Hlg with Re(CO)5Na and Mn(CO)5K is an additional supporting evidence of the assumed mechanism.