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Topic: confusion with this reagent  (Read 2503 times)

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Offline rlabomba

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confusion with this reagent
« on: November 27, 2017, 11:12:23 AM »
Hi There,
I'm confused as to what reagent is used to complete this reaction.

My thinking is:
1) NaNH2
2) CH3I

To add the extra methyl
« Last Edit: November 27, 2017, 11:27:56 AM by rlabomba »
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Offline rlabomba

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Re: confusion with this reagent
« Reply #1 on: November 27, 2017, 11:23:39 AM »
My thinking is:
1) NaNH2
2) CH3I

To add the extra methyl
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Offline rolnor

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Re: confusion with this reagent
« Reply #2 on: November 27, 2017, 11:41:52 AM »
The Simmons-Smith reagent ZnCH2I could be used, or diazomethane and catalyst like PdOAc2 I think. I have done many cyclopropanations with ethyl diazoacetate and PdOAc2.
I have not seen your suggestion with CH3I and NaNH2.
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Offline rlabomba

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Re: confusion with this reagent
« Reply #3 on: November 27, 2017, 11:43:52 AM »
yeah, This is for alkynes not alkenes.  my thinking is incorrect.  I'll check out The Simmons-Smith reagent.  Thanks!
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Offline clarkstill

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Re: confusion with this reagent
« Reply #4 on: December 01, 2017, 05:11:43 AM »
Or you can do CHCl3, aq. KOH, NBu4Cl (to form dichlorocarbene) then do a zinc reduction of the dichlorocyclopropane you form
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