The kinetics of reaction of [Fe(η 5 -C 5 H 5 )(CO) 2 CH 2 SPh 2 ]BF 4 with cyclooctene in CH 2 Cl 2 solution have been studied under pseudo-first-order conditions at room temperature. The variation of k obs is nonlinear in both cyclooctene and added Ph 2 S. The results are interpreted in terms of a two-step reaction in which the cation [Fe(η 5 -C 5 H 5 )(CO) 2 CH 2 SPh 2 ] + undergoes reversible, dissociative loss of Ph 2 S followed by competitive capture of the methyleneiron complex by cyclooctene to produce bicyclo[6.1.0]nonane. The methyleneiron intermediate is 4-5 times more reactive toward diphenylsulfide than cyclooctene. In the absence of added Ph 2 S, millimolar solutions of the iron complex react with cyclooctene at room temperature with a half-life of about 36 min to give >85% yields of bicyclo[6.1.0]nonane after 3 h, and it is thus more reactive than the dimethyl-and methylphenylsulfonium salt analogues.
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