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Mechanism for this reaction

Im not sure about the mechanism for this reaction.. i've given the final product below, I don't know what happens to the oxygens or hydrogen on the nitrogen

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Reply 1
What solvent/conditions are you using?

That is deffo your final product?
Reply 2
Original post by Pigster
What solvent/conditions are you using?

That is deffo your final product?


This image has all the information we've been given
Reply 3
The attack from the lone pair on the N to the C of C=O would end up making an imine!
Reply 4
Original post by Pigster
The attack from the lone pair on the N to the C of C=O would end up making an imine!


yes ive drawn it wrong, i still don't understand where the oxygen goes though :/
Reply 5
So, what were you given? the nitrodiketone start point and the heterocyclic product?
Reply 6
Original post by Pigster
So, what were you given? the nitrodiketone start point and the heterocyclic product?


yes
Reply 7
Original post by jacksonmeg
yes


You need to transform the carbonyls into something which is a good leaving group.
Reply 8
Original post by alow
You need to transform the carbonyls into something which is a good leaving group.


i was thinking of H2O+ groups but i don't know if to just presume there will be water or H+ in solvent
Reply 9
Original post by jacksonmeg
i was thinking of H2O+ groups but i don't know if to just presume there will be water or H+ in solvent

Or just do reductive amination. Your choice.

For an SN2 I wouldn't add protons, as the amino group would be protonated and make the amine lone pair a pretty bad nucleophile. What R-OX groups do you know that are good leaving groups?

Does the reaction have to be stereoselective?
(edited 7 years ago)
Original post by alow
Or just do reductive amination. Your choice.

For an SN2 I wouldn't add protons, as the amino group would be protonated and make the amine lone pair a pretty bad nucleophile. What R-OX groups do you know that are good leaving groups?


i dont think i can, i just have to do the mechanism for the reaction they listed
Original post by alow
Or just do reductive amination. Your choice.

For an SN2 I wouldn't add protons, as the amino group would be protonated and make the amine lone pair a pretty bad nucleophile. What R-OX groups do you know that are good leaving groups?

Does the reaction have to be stereoselective?


I think so, but i dont need to explain the steroselectivity. I cant think of any leaving groups you could make with no conditions giving...
Reply 12
Original post by jacksonmeg
i dont think i can, i just have to do the mechanism for the reaction they listed


What exactly have they given you? You can't just write a mechanism if you don't know the reagents.

Original post by jacksonmeg
I think so, but i dont need to explain the steroselectivity. I cant think of any leaving groups you could make with no conditions giving...


Never heard of a tosylate?
Original post by alow
What exactly have they given you? You can't just write a mechanism if you don't know the reagents.



Never heard of a tosylate?


hang on ill get the full question
Original post by alow
What exactly have they given you? You can't just write a mechanism if you don't know the reagents.



Never heard of a tosylate?


full question
Reply 15
Original post by jacksonmeg
full question


Okay. What will H2 / Pd / C do to a carbonyl?
Original post by jacksonmeg
full question


Hydrogenation of imine / iminimum intermediates. This will also explain relative stereochemistry.
Original post by alow
Okay. What will H2 / Pd / C do to a carbonyl?


reduce to alcohol?
Original post by TeachChemistry
Hydrogenation of imine / iminimum intermediates. This will also explain relative stereochemistry.


i havent made a imine intermediate ... i dont know how to get there
Reply 19
Original post by jacksonmeg
reduce to alcohol?


Nope. It won't do much, unless you give it a lot of time.

Original post by jacksonmeg
i havent made a imine intermediate ... i dont know how to get there


Assume you have a protic solvent/proton donor.

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