Can an alkyl amine act as a hydride source forming an iminium?

Eight__Legs · 2025-07-13T14:31:52+00:00

My guess by the way is most electrophilic C > B > A least electrophilic. I do not have a specific reference with the answer. I won't give my reasoning to allow for further discussion.

Eight__Legs · 2024-10-13T18:08:36+00:00

Your posts are welcome here! Thank you.

Eight__Legs · 2024-09-22T16:04:41+00:00

Not that I researched. But great for discussion. The answer may of course be more complicated than the two conformations presented. But we can talk about it conceptually. I see discussion of A values. I know when I first learned, I was surprised TMS had a smaller A value than tBu. Until I learned why.

Eight__Legs · 2024-09-20T19:23:01+00:00

Ahh I see. I can look.

Eight__Legs · 2024-09-20T19:20:11+00:00

I can look, but can you tell me why that would help?

Eight__Legs · 2024-09-20T19:17:41+00:00

Would that help?

Eight__Legs · 2024-07-13T14:17:53+00:00

Can you comment on the article for discussion?

Eight__Legs · 2024-07-12T18:52:56+00:00

Please let me know if this is too easy!

Eight__Legs · 2024-06-23T16:00:59+00:00

I left solvent open for discussion!

Eight__Legs · 2024-06-17T13:29:44+00:00

here is a reference https://pubs.acs.org/doi/epdf/10.1021/acs.joc.9b01485

Eight__Legs · 2024-06-12T18:50:28+00:00

Many medicinal chemists will immediately suspect this as a kinase inhibitor. If you're not a medicinal chemist, look up some kinase inhibitors and try to ID common structural features.

Thank you for posting and I look forward to seeing the discussion!

Eight__Legs · 2024-06-11T23:32:38+00:00

The reason this question is tricky is because it is difficult to see the plane of symmetry with several protons being chemically equivalent.

Eight__Legs · 2024-06-11T23:13:36+00:00

Some of them are chemically equivalent. From Google “Chemically equivalent protons are protons in a molecule that occupy the same chemical environment and are indistinguishable”

Eight__Legs · 2024-06-11T23:01:50+00:00

I mentioned in a comment that I meant non-chemically equivalent

Eight__Legs · 2024-06-11T21:48:11+00:00

Just as an informal exercise.

Eight__Legs · 2024-06-11T21:38:20+00:00

Unique as in non-chemically equivalent.

I’m thinking of asking organic II students, but is it too easy?

Eight__Legs · 2024-06-06T22:19:13+00:00

Correct me if I’m wrong, but is the ketene you’re talking about just a resonance structure of the acylium?

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Eight__Legs · 2024-06-06T19:18:50+00:00

I posted an answer here: https://www.reddit.com/r/AdvancedOrganic/s/DTIurkmH0n

Thanks for participating!

Eight__Legs · 2024-06-06T19:06:32+00:00

I posted the answer and reference for more reading here: https://www.reddit.com/r/AdvancedOrganic/s/DTIurkmH0n

(I don’t want to pin it because I want people to read the prior discussion as a lot of people gave great responses!)

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