Timeline for Complete mechanism of benzotriazole synthesis from o-phenylenediamine
Current License: CC BY-SA 4.0
12 events
| when toggle format | what | by | license | comment | |
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| Jan 18, 2022 at 12:36 | vote | accept | CommunityBot | ||
| Jan 17, 2022 at 7:55 | history | became hot network question | |||
| Jan 17, 2022 at 6:53 | history | edited | andselisk♦ | CC BY-SA 4.0 |
deleted 3 characters in body; edited tags; edited title
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| Jan 17, 2022 at 1:03 | answer | added | user55119 | timeline score: 4 | |
| Jan 17, 2022 at 0:45 | comment | added | user55119 | Jacob, you are free to like what you like. I'm not convinced. I'll post an answer. | |
| Jan 17, 2022 at 0:13 | comment | added | user102173 | ibb.co/Lzthh3G | |
| Jan 17, 2022 at 0:07 | comment | added | user102173 | The amino-to-diazo electrocyclization and 1,2 shift is interesting, but I think I like Mithoron's answer where structure 5's nitrogen displaces water and then deprotonates better. | |
| Jan 16, 2022 at 23:59 | comment | added | user102173 | When I was drawing it I figured the electrocyclization through the electronegative N wouldn't work but ended up drawing it anyway. So I was right to be concerned. | |
| Jan 16, 2022 at 23:58 | comment | added | user55119 | Your solution is plausible but I am bothered by the use of structure 7 the way you have. Its too far to reach! If you do an electrocyclization of 7 to form the benzene ring and a 4-membered ring bearing vicinal nitrogens, then you can have the remaining nitrogen as a neutral "nitrene" ready for 1,2-shift of nitrogen and ring expansion. OTOH, acid-catalyzed cyclization of structure 2 followed by dehydration gets you there. | |
| Jan 16, 2022 at 23:55 | comment | added | user102173 | You mean the intermediate with the pendant hydronium would cyclize with expulsion of water? | |
| Jan 16, 2022 at 23:54 | comment | added | Mithoron | Too many steps, amino could substitute H2O, then deprotonation. | |
| Jan 16, 2022 at 23:02 | history | asked | user102173 | CC BY-SA 4.0 |