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#1 2010-05-17 00:25:19

orgopete
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Hydroboration-oxidation methylcyclohexene ->trans-2-methylcyclohexanol

The R-groups of borane can be intermediate alkyl groups or hydrogen, depending on the stage of hydroboration reaction. The complete formation of a trialkylborane is in A Guide to Organic Chemistry Mechanisms. This or similar examples are popular subjects for examinations as it shows the stereochemistry of the hydroboration reaction (syn addition) and the stereochemistry is retained in the oxidation step to give the trans-2-methylcyclohexanol.

          http://www.curvedarrow.com/chem/ZZ26DC8999.jpg

This example is excerpted from A Handbook of Organic Chemistry Mechanisms, available at http://www.curvedarrowpress.com/ or Amazon.com

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