Timeline for Pyridine synthesis by tin(II) chloride reduction of 5-nitronorbornene
Current License: CC BY-SA 4.0
14 events
| when toggle format | what | by | license | comment | |
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| Aug 12, 2020 at 19:24 | comment | added | Mathew Mahindaratne | @orthocresol: Good point. Why I didn't think thay before? Now, I don't have any doubts. | |
| Aug 12, 2020 at 12:32 | history | edited | user55119 | CC BY-SA 4.0 |
edited body
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| Aug 12, 2020 at 12:27 | comment | added | user55119 | @orthocresol: Good point. Done | |
| Aug 12, 2020 at 12:26 | history | edited | user55119 | CC BY-SA 4.0 |
Reconfigured loss of acetaldehyde in diagram 2
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| Aug 12, 2020 at 7:01 | comment | added | orthocresol | Mostly a quibble, but I was wondering if the last step could be conveniently drawn as such. A bit reminiscent of beta-ketoacid decarboxylation. i.sstatic.net/Byn29.jpg (cc @MathewMahindaratne) | |
| Aug 11, 2020 at 22:56 | history | edited | user55119 | CC BY-SA 4.0 |
Split last sentence into two.
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| Aug 9, 2020 at 21:33 | comment | added | Mathew Mahindaratne | Might not. Otherwise, the last elimination step would have been reversible. I think gaining aromatically is a very good point for the elimination. In my experience, I didn't find any decomposition of $\beta$-amino acids during their synthesis. | |
| Aug 9, 2020 at 20:29 | comment | added | user55119 | @Mathew: I've thinking about your question again. There are stannic salts generated in the reduction. Perhaps they facilitate loss of acetaldehyde. So the question is, will Sn(IV) catalyze the addition of acetaldehyde to 3-phenylpyridine (9) to form 8? | |
| Aug 9, 2020 at 17:25 | comment | added | user55119 | @Mathew: Wouldn't be surprised if the zwitterion of beta-aminopropionic acid gives ethylene under some set of conditions. In the present case, becoming aromatic is certainly worth something. If you mix 9 and 10 under some set of conditions, I'd be surprised to see any 8. | |
| Aug 9, 2020 at 17:00 | comment | added | Mathew Mahindaratne | I already upvoted your answer. But I'm curious about the elimination of acetaldehyde. What is the driving force? Is that mean $\beta$-amino acids are prone to leave $\ce{CO2}$? | |
| Aug 8, 2020 at 21:45 | history | edited | user55119 | CC BY-SA 4.0 |
added 2 characters in body
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| Aug 8, 2020 at 20:13 | history | edited | user55119 | CC BY-SA 4.0 |
Added a stereochemical explanation
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| Aug 8, 2020 at 3:25 | history | edited | user55119 | CC BY-SA 4.0 |
added 12 characters in body
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| Aug 8, 2020 at 3:20 | history | answered | user55119 | CC BY-SA 4.0 |
