Topic: Reduction of Conjugated carbonyl group (Read 3842 times)

bmthog · « **on:** October 18, 2011, 08:53:12 PM »

Could Li/NH3 reduce carbonyl group in conjugated C=C-C=O to C=C-CH2 like Clemmensen?

bmthog · « **Reply #1 on:** October 19, 2011, 11:30:50 PM »

Anybody please help me

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discodermolide · « **Reply #2 on:** October 20, 2011, 01:25:00 AM »

Quote from: bmthog on October 18, 2011, 08:53:12 PM

Could Li/NH3 reduce carbonyl group in conjugated C=C-C=O to C=C-CH2 like Clemmensen?

I guess these conditions will reduce the entire thing to the corresponding alcohol.
If you want to reduce the carbonyl group only use DIBAL-H at low temperature.

Honclbrif · « **Reply #3 on:** October 20, 2011, 07:26:18 AM »

I believe Birch conditions will form an enolate from an a,b-unsaturated carbonyl. If you want to selectively reduce the carbonyl to an allylic alcohol, try the Luch reduction.

orgopete · « **Reply #4 on:** October 20, 2011, 08:50:56 AM »

Quote from: bmthog on October 18, 2011, 08:53:12 PM

Could Li/NH3 reduce carbonyl group in conjugated C=C-C=O to C=C-CH2 like Clemmensen?

No.

What is the real question? Is it how could that transformation be carried out?

Topic: Reduction of Conjugated carbonyl group (Read 3842 times)

bmthog

Reduction of Conjugated carbonyl group

bmthog

Re: Reduction of Conjugated carbonyl group

discodermolide

Re: Reduction of Conjugated carbonyl group

Honclbrif

Re: Reduction of Conjugated carbonyl group

orgopete

Re: Reduction of Conjugated carbonyl group

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