Abstract
Triphenyl-, diphenylmethyl-, and phenyldimethylsilyl-lithium react very rapidly with 9-phenylfluorene in tetrahydrofuran (THF) but the reaction can be followed spectroscopically using the stop-flow technique at low temperatures. The order of reaction, found from the dependence of the initial rate of reaction on the initial reactant concentrations, is unity in both 9-phenylfluorene and the relevant organosilyl-lithium reagent. The thermodynamic constants of activation for the reaction between 9-phenylfluorene and triphenylsilyl-lithium (Ph3SiLi), diphenylmethylsilyl-lithium (Ph2MeSiLi), and phenyldimethylsilyl-lithium (PhMe2SiLi), respectively, are: ΔH≠ = 4.5, 4.0, and 4.0 kcal mol−1; ΔG≠ = 13.0, 12.5, and 12.5 kcal mol−1; ΔS≠ = −34.9, −34.8, and −34.9 cal mol−1 deg−1
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