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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: xshadow on November 21, 2020, 03:29:14 PM

Title: C=O reduction in presence of C=C bond
Post by: xshadow 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

Title: Re: C=O reduction in presence of C=C bond
Post by: rolnor on November 22, 2020, 04:04:11 AM

I think you can use a deactivated Raney-Ni to reduce dithioacetal without reducing the alkene.

Title: Re: C=O reduction in presence of C=C bond
Post by: xshadow on November 22, 2020, 02:53:25 PM

Quote from: rolnor on November 22, 2020, 04:04:11 AM

I think you can use a deactivated Raney-Ni to reduce dithioacetal without reducing the alkene.

ook ,thanks!