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Hydroboration and Organic Synthesis pp 17–58Cite as

Kinetic Studies

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Abstract

Kinetic studies provide valuable information in the areas of both mechanistic and synthetic chemistry concerning the effects of substituents in alkenes and alkynes. The effects of substituents that donate or withdraw or polarize electrons of C=C or C≡C provide information regarding the mechanism of hydroboration. On the other hand, relative rates of hydroboration of substituted or unsubstituted C=C or C≡C give synthetic chemists improved means of predicting the selective hydroboration of C=C or C≡C or their functionalized derivatives. 9-BBN has proven to be the best candidate for the investigation of mechanism and kinetics of hydroboration because:

  1. 1.

    It has high thermal stability and purity.

  2. 2.

    It is convenient to handle compared to other boranes as it has lower sensitivity to oxygen and water vapors.

  3. 3.

    With only one center per boron, its overall reaction with an alkene involves only one dissociation step and one hydroboration step; in contrast, borane (BH3) has three consecutive addition reactions, three redistribution equilibria, and five monomer-dimer equilibria [1].

  4. 4.

    9-BBN reactions can be studied in solvents such as carbon tetrachloride, cyclohexane, and benzene whereas 9-BBN exists exclusively as dimer, thus eliminating complexation [2] with solvents and simplifying the kinetics.

  5. 5.

    9-BBN is highly regio- and stereoselective, which assures the study of only one reaction.

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© 2007 Springer-Verlag Berlin Heidelberg

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(2007). Kinetic Studies. In: Hydroboration and Organic Synthesis. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-49076-0_4

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