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Hydroboration–oxidation

2 real reactions from the literature, on terminal alkynes and trisubstituted five-membered cycloalkenes. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Hydroboration: 1-hexyne (a terminal alkyne) with 1); 2) NaOH / H2O2 gives hexanal (the anti-Markovnikov product).

  2. Hydroboration: 1-methylcyclopentene (a trisubstituted five-membered cycloalkene) with BH3•SMe2; 1); 2) NaOH / H2O2 gives 2-methylcyclopentanol (the anti-Markovnikov product).