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@rojaslab For next week, I propose a curtius rearrangement upon heating of the acyl azide to form the isocyanate. Then, a nucleophilic attack from the alkene to the isocyanate forming a six membered ring. The nitrogen is then protonated forming the amide. Which then leads to the opening of the cyclopropane using water as base to abstract the hydrogen alpha to the nitrogen. Opening the ring, sequestering the carbocation formed in the second step, and forming two pi bonds and the final 7 membered ring. Giving the product.
Please always ask me questions! Typically, most reactions I post are real and possible. When possible, I even include the publication that reported the reaction. In this case, it was more of a theoretical exercise.
In which research article could I find this reaction or mechanistic study of this reaction? I can only find the thermal decomposition, hydroperoxy radical mediated decomposition, photodegredation and whole bunch of other things. Also, what about making a tert-butyl carbocation and making tert-butyl alcohol?
I do not. I'm sure the hydroxyl group acting as an electron-donating group is what drives this reaction. The extra stabilization of the sigma complex it affords.
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How did you do? I'd love to hear your proposals for next week's mechanism so drop them down below! Subscribe for more chemistry content, and hit the notification bell to stay updated! #ScienceCommunity #MechanismMonday #OrganicChemistry
Underrated creator
You’re too kind! 🙏🏽
in the last step it feels more like an E1 mecanism since water is not a good base and also the formed carbocation is tertiary and so it is "stable"
Haha. More stable than a primary carbocation, for sure! But lower in energy doesn’t mean eternally persistent!
@rojaslab wdym ? Once the tertiary carbocation is formed. Thats when the water attacks a proton to make the alkene
Thank you man, you save my Mondays
Ah that’s so nice to hear! I’m grateful that you pop in to watch!
Very similar to BOC deprotection mechanism.
Yasssss!!! Nice catch on that. And geez, you were so fast this week!
@rojaslab For next week, I propose a curtius rearrangement upon heating of the acyl azide to form the isocyanate. Then, a nucleophilic attack from the alkene to the isocyanate forming a six membered ring. The nitrogen is then protonated forming the amide. Which then leads to the opening of the cyclopropane using water as base to abstract the hydrogen alpha to the nitrogen. Opening the ring, sequestering the carbocation formed in the second step, and forming two pi bonds and the final 7 membered ring. Giving the product.
@@abs0lute-zer061 Ayyyy nice work! I wonder how many people have heard of the Curtius rearrangement
Can i ask the question? Do the reaction really occur and the yield of the reaction is huge enough ?
Please always ask me questions! Typically, most reactions I post are real and possible. When possible, I even include the publication that reported the reaction. In this case, it was more of a theoretical exercise.
In which research article could I find this reaction or mechanistic study of this reaction? I can only find the thermal decomposition, hydroperoxy radical mediated decomposition, photodegredation and whole bunch of other things. Also, what about making a tert-butyl carbocation and making tert-butyl alcohol?
I actually don't know of any off the top of my head. In theory, most reactions are reversible though via the principle of microscopic reversibility.
Do you suppose this mechanism would still be vaild for tert-butyl benzene.
I do not. I'm sure the hydroxyl group acting as an electron-donating group is what drives this reaction. The extra stabilization of the sigma complex it affords.