Abstract
When a solution of biphenylene in trifluoroacetic acid containing mercury(II) trifluoroacetate is photolysed with ultraviolet light, the ESR spectra show the progressive mercuration of the biphenylene radical cation in the β-position. β-Proton hyperfine coupling [ a(H β) 3.58 G] is lost, and 199Hg primary, secondary, and tertiary satellites [ a( 199Hg β) 76–77 G] appear untl tetra-β-mercuration is complete. It is concluded that, apart from the usual electrophilic mechanism, an alternative mechanism for mercuration exists, and that this probably involves collapse of the aromatic radical cation, ArH +., with its counterion, HgX 2 -.: ArH + HgX 2 → ArH +. + HgX 2 → HAr H − X 2 → ArHgX + HX
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