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The current reaction scheme appears to be for the Ing-Manske procedure, not the Gabriel Synthesis. Haligonian1 20:44, 16 August 2006 (UTC)
Agreed, the Gabriel Synthesis has just acid work up at the end and is slower than the Ing-Manske procedure. 8 May 2008 —Preceding unsigned comment added by 129.67.110.171 (talk) 11:36, 8 May 2008 (UTC)
"The reaction fails with secondary alkyl halides" - really???
The person who made the scheme for the mechanism is practically chemically illiterate. — Preceding unsigned comment added by 73.15.21.218 (talk) 10:21, 24 January 2015 (UTC)
- Disagree, a chemical illiterate would not know the difference between nitrogen and oxygen. This is disrespectful towards the contributing editor. The image is flawed with respect to some of the arrows going around. Would the image depicted in the German-language version be acceptable? V8rik (talk) 23:11, 24 January 2015 (UTC)
Mechanism
editHere's a JOC paper talking about the most likely mechanism. J. Org. Chem., 1995, 60 (14), pp 4536–4541 The scheme shown in this article, along with that shown in the German language wikipedia, seem to imply that there is a negatively-charged nitrogen when the five-membered ring breaks. This is (by far) not the most stable resonance model for this molecule. The negative charge should properly reside on the oxygen.
I may draw up a complete mechanism in the future. Feel free to correct me or point me to other literature in the meantime.
— Preceding unsigned comment added by 68.65.169.22 (talk) 00:52, 17 August 2017 (UTC)
- Great tip. I am going to remove the mechanism picture (other editors might revert my change), since it is overly detailed and, ineptly (run-on reactions) mixes in the hydrazine deprotection step. My advice would be to describe the JOC result in a few words, check to see if the textbooks have picked up on this report (in which case cite the textbook, not JOC per WP:SECONDARY). Be careful about molecule, ion, and ion-pairing. Keep looking around for other areas worth improving.--Smokefoot (talk) 02:13, 17 August 2017 (UTC)