The leaving group is crucial in determining the ease with which the phenyl cation is generated. A good leaving group should be able to stabilize the negative charge that forms upon its departure. Common leaving groups include halides (Cl?, Br?, I?), tosylates (TsO?), and mesylates (MsO?).
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2-(2,2,2-trifluoroethoxy)-5-methoxytrimethylsilylbenzene
Diphenylmethyl-dichlormethyl-sulfon
cyanoacetate
