December 01, 2020, 10:03:21 PM
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Topic: C=O reduction in presence of C=C bond  (Read 178 times)

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Offline xshadow

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C=O reduction in presence of C=C bond
« on: November 21, 2020, 03:29:14 PM »
How can  reduce the C=O bond  in the presence of C=C bonds NOT conjugated to carbonyl ??

For example:

CHO-CH2-CH2-HC=CH-CH=CH2 ?

Ps: reduce C=O to CH2 , not to alcohol

Can I use wolff kishner?
I suppose I can't use hydrogenation because of C=C
Also NaBH4  is not good here because I get an alcohol. Not a total reduction

Another way can be mozingo reaction? Using a dithiol and then Ni raney...but I don't know if also the C=C will be reduced...usually H2 with Ni raney can reduce alkenes

Thanks
« Last Edit: November 21, 2020, 06:25:26 PM by xshadow »

Offline rolnor

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Re: C=O reduction in presence of C=C bond
« Reply #1 on: November 22, 2020, 04:04:11 AM »
I think you can use a deactivated Raney-Ni to reduce dithioacetal without reducing the alkene.

Offline xshadow

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Re: C=O reduction in presence of C=C bond
« Reply #2 on: November 22, 2020, 02:53:25 PM »
I think you can use a deactivated Raney-Ni to reduce dithioacetal without reducing the alkene.

ook ,thanks!

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