Anisole is cleaved by bis(trimethylsilyl)mercury at 185°; some dimethylmercury is formed, and the major organic product is phenoxytrimethylsilane, which may be formed in a four-centre process in which a Me–Hg bond is simultaneously produced. Little, if any, attack on anisole by trimethylsilyl radicals occurs. Corresponding reactions, involving the cleavage of C6H11–O and Me–O bonds occur with methoxycyclohexane, the major organic products being the compounds Me3SiOMe and Me3SiOC6H11, in roughly 3 : 1 ratio, and cyclohexane, the latter presumably coming from cyclohexyl radicals formed by dissociation of C6H11–Hg bonds. Analogous cleavages occur with ethoxybenzene, methoxytrimethylsilane, and cyclohexoxytrimethylsilane, but with diphenyl ether the greatly dominant reaction is the decomposition of the mercurial to hexamethyldisilane. The results with anisole indicate that radical processes may be less important than has been suggested, and molecular reactions correspondingly more important, in reactions of the mercurial with other aromatic compounds such as chloro- and bromo-benzene.