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Topic: What is this reaction called and how does it work?  (Read 7170 times)

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Offline kims

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What is this reaction called and how does it work?
« on: April 01, 2008, 01:29:14 AM »
a
« Last Edit: April 04, 2008, 10:58:41 PM by kims »
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Offline Rabn

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Re: What is this reaction called and how does it work?
« Reply #1 on: April 01, 2008, 04:47:42 AM »
Dude...you need to start by identifying what the solution is composed of and work from there. Draw each structure and consider the functional groups of each.  Lithium is only used in certain mechanisms, could be a clue.
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Offline phil81

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Re: What is this reaction called and how does it work?
« Reply #2 on: April 01, 2008, 05:53:24 AM »
I'm not sure about the name of the first reaction, but the mechanism should be similar to a Swern oxidation. Look that one up.

About the second: What is the reactivity of organometallic reagents? Of organolithium reagents? Of acetylenes?
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Offline Rico

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Re: What is this reaction called and how does it work?
« Reply #3 on: April 01, 2008, 07:15:22 AM »
yes the first reaction is very similar to the Swern oxidation and it is called the Parrikh-Doering oxidation.

Rico
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Offline kims

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Re: What is this reaction called and how does it work?
« Reply #4 on: April 01, 2008, 09:38:47 AM »
Can anyone tell me what the lithium reagent is called? I don't know how to name it?
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Offline ARGOS++

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Re: What is this reaction called and how does it work?
« Reply #5 on: April 01, 2008, 10:18:36 AM »

Dear Dakims;

TMS        =    TriMethylSilyl ─
─C≡C─      =    Ethinyl─,   or Acetylide─
Li            =    Lithium
              =     ?;            ─  OR:    Lithium(TMS)- Acetylide.

Good Luck!
                    ARGOS++

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Offline kims

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Re: What is this reaction called and how does it work?
« Reply #6 on: April 01, 2008, 01:12:24 PM »
a
« Last Edit: April 04, 2008, 10:58:52 PM by kims »
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Offline kims

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Re: What is this reaction called and how does it work?
« Reply #7 on: April 02, 2008, 04:49:25 PM »
anyone?
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Offline sjb

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Re: What is this reaction called and how does it work?
« Reply #8 on: April 03, 2008, 11:09:53 AM »
Is this all one reaction, so you have the Weinreb amide going to the alcohol, which is then Parrikh-Doering oxidised and the organometallic adding to the product?

I thought Weinreb amides added to organolithiums to give the ketone, so I'm a bit confused..
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Offline kims

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Re: What is this reaction called and how does it work?
« Reply #9 on: April 03, 2008, 04:40:14 PM »
oh sorry, there is one reaction on the top and there is a second one.
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Offline sjb

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Re: What is this reaction called and how does it work?
« Reply #10 on: April 05, 2008, 02:51:48 PM »
Is there anything in the original P-D paper?

Parikh, J. R.; Doering, W. von E.; J. Am. Chem. Soc. 1967, 89, 5505.

http://dx.doi.org/10.1021/ja00997a067

S
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