Cyclopropane ring mercury compounds

Oxymercuration of simple alkyl- and acyl-substituted cyclopropenes generally results in ring opening.Addition of mercury(II) acetate to 3-methyl-3-phenylcyclopropene, however, gave a low yield of a cyclopropane containing organomercury compound (15-20%), which was converted into an isomeric mixture of 1 -methoxy-2-methyl-2-phenylcyclopropanes by reduction with lithium aluminum hydride. Reaction of 5 with mercury trifluoroacetate in methanol and then sodium hydroxide led predominantly to one cylopropane. ... 

The stereochemistry of the ring-opening reaction of exo- and e (7o-tricyclo[3.2.1.0 " ]octane 41 by proton, deuterium and mercury(II) ions has been investigated. When the e t/o-isomer was treated with methanol in the presence of a catalytic amount of p-toluenesulfonic acid, endo-2-methoxybicyclo[3.2.1]octane (42a) was obtained in high yield. The exo-compound reacted in an analogous fashion to give exo-2-methoxybicyclo[3.2.1]octane (44a) as the major product and exo-2-methoxy- yn-7-methylbicyclo[2.2.1]heptane (45 a) which resulted from the cleavage of an outside cyclopropane bond. 

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