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Topic: What does H2O2, NaOH do in this reaction?  (Read 20049 times)

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Offline brasarehot

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What does H2O2, NaOH do in this reaction?
« on: October 26, 2010, 11:00:16 AM »
Cyclohexanone to 1-cyclohexyl 1-pentanol. 1) (C6H5)3P=CHCH2CH2CH2CH3; 2) BH3, THF; 3) H2O2, NaOH.
It seems to me you get the product after BH3, so why is H2O2 there?
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Offline discodermolide

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Re: What does H2O2, NaOH do in this reaction?
« Reply #1 on: October 26, 2010, 11:13:57 AM »
Quote from: brasarehot on October 26, 2010, 11:00:16 AM
Cyclohexanone to 1-cyclohexyl 1-pentanol. 1) (C6H5)3P=CHCH2CH2CH2CH3; 2) BH3, THF; 3) H2O2, NaOH.
It seems to me you get the product after BH3, so why is H2O2 there?

This is a classical hydroboration of a double bond, which requires oxidation of the borinic acid ester intermediate, take it from there
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Offline orgopete

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Re: What does H2O2, NaOH do in this reaction?
« Reply #2 on: October 28, 2010, 11:09:07 PM »
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