Author Topic: Grignard variations, these work?  (Read 768 times)

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alchemy_bee

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Grignard variations, these work?
« on: April 29, 2002, 05:19:00 AM »
I was looking at this novle route to p2p:


This also caught my eye:


Phenyl-2-Propanone from Benzylchloride (via Bn2Zn or Bn2Cd)
2 PhCH2MgCl + CdCl2 => (PhCH2)2Cd + 2 MgCl2
(PhCH2)2Cd + Ac2O => 2 PhCH2COCH3 + CdO
...80-90% yield




Would somthing like this work?



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alchemy_bee

  • Guest
also
« Reply #1 on: April 29, 2002, 05:41:00 AM »
Also if you imine magnesium salt (=NMgCl), would Methyl Chloride gas substitute in to yield a  =N-CH3 + MgCl2?

This would be great, sort of a double grignard if starting from Benzyl chloride + Mg + acetonitrile to give the  intermediate phenyl-2-propanone imine magnesium salt, expose to Methyl Chloride gas and then reduce.

Inputs please





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Rhodium

  • Guest
Nope, none of your proposed reactions work.
« Reply #2 on: April 29, 2002, 07:20:00 AM »
Nope, none of your proposed reactions work.

Bozakium

  • Guest
OrganoCadmium
« Reply #3 on: April 29, 2002, 08:39:00 PM »
Alchummybee: If you like playing with organocadmium compounds, I put one up on the meth synth contest thread a few mos. back. Theyre from a textbook so might bee viable.
--Bz138

alchemy_bee

  • Guest
Bozakium: I was just going down phenylacetone.
« Reply #4 on: April 30, 2002, 12:58:00 AM »
Bozakium: I was just going down phenylacetone.html on Rhodiums site looking for new ideas.

Grignard reactions are very interesting technology. Using somthing as simple as benzyl chloride as a starting material and getting p2p in reasonable yield is awsome.

I dont know much about chemistry yet but have desier to understand all the mechanisms in detail of the reactions im reading and learn as i go.

After a weekend of brewing up that idea the next thing i would like to know is why =NMgCl group and no longer be tweeked with while maintaining the imine.

Using NaBH4 on the imine Mg salt is a great one pot prosedure to benny, Im very interseted to find out if there is any way to use the nature of imine salt to add a methyl group in such a one pot way



Can a bee be visa vis its entity when half a bee philosophically must ipso facto half not be?

alchemy_bee

  • Guest
Alright, what about this: if i just had PhCH2MgCl ...
« Reply #5 on: April 30, 2002, 01:11:00 AM »
Alright, what about this: if i just had PhCH2MgCl and exposed to methyl chloride gas would it kick off the grignard set and add CH3 to the end?



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alchemy_bee

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http://alchemybee.topcities.com/idea.
« Reply #6 on: April 30, 2002, 01:36:00 AM »
would somthing like this work, if there was such a chemical?

Can a bee be visa vis its entity when half a bee philosophically must ipso facto half not be?

Rhodium

  • Guest
grignard
« Reply #7 on: April 30, 2002, 02:47:00 AM »
No, the grignard reagent would just abstract the hydrogen from the amine, forming toluene and the MgCl salt of the amine.

I'd suggest you stop guessing what grignard reagents react with or not, and read up on it instead. Everything you want to know can be found by using Google, with the search terms "grignard" together with "reaction" or "reagent".


foxy2

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hmmm
« Reply #8 on: April 30, 2002, 04:59:00 AM »
If that H was replaced with a benzyl or benzoyl it might work. 
That would make it more diffucult than the conventional methods.

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Rhodium

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N-tosyl-2-methylaziridine
« Reply #9 on: April 30, 2002, 01:02:00 PM »
My favorite is the reaction of PhMgBr with N-tosyl-2-methylaziridine for the 1-step synthesis of amphetamine (this can be made in a stereocontrolled manner, not too expensive). I wonder if the reaction of PhMgBr with (S)-1,2-dimethylaziridine would give d-meth directly in one step?

alchemy_bee

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Rhod: What is N-tosyl-2-methylaziridine and ...
« Reply #10 on: April 30, 2002, 06:17:00 PM »
Rhod: What is N-tosyl-2-methylaziridine and (S)-1,2-dimethylaziridine i cant find it on chemfinder or google. thanks



Can a bee be visa vis its entity when half a bee philosophically must ipso facto half not be?

Rhodium

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Aziridine grignard
« Reply #11 on: April 30, 2002, 07:42:00 PM »
Speciality chemicals (you would likely have to make them yourself). An aziridine is a three-membered ring with one nitrogen and two carbons (the nitrogen bearing the 1-position). A tosyl group is 4-Methylbenzenesulfonate (4-CH3-C6H4-SO2-). UTFSE for aziridine for more discussions on this subject.