Talk:Schmidt reaction

1923 or 1924

Schmidt, K.F.: Angew. Chem. 36, 1923, 511 is also listed as article for the Schmidt reaction. S discovered 1923.--Stone (talk) 18:50, 4 April 2008 (UTC)

Mechanism 1, intermediate 2

I feel that as drawn, the curly arrows on intermediate 2 are somewhat confusing, especially to those who are new to this class of arrangements. I assume that the mechanism as depicted suggests that lone pair of the nitrogen bonded to carbon is pushed to the C-N bond. This means the tail of the arrow should be positioned over the nitrogen, not the nitrogen-nitrogen single bond. As drawn, it seems to imply that the diazonium is acting as the electrofuge, when in reality it's invariably a nucleofuge. Either way, I think the lone pair need not be explicitly invoked in this scenario, as one could simply draw the R group migrating to nitrogen concurrent with the elimination of N2, which will also lead to a resonance form of 3. --129.105.149.247 (talk) 21:35, 11 August 2015 (UTC)

I agree. One of the arrows for the R-migration step in Mechanism 1 is just wrong. — Preceding unsigned comment added by 143.167.200.42 (talk) 14:06, 17 June 2019 (UTC)

Mechanism 1

The first step in the mechanism showing conversion of a carboxylic acid into an amine is incorrect. Protonation of a carboxylic acid occurs at the carbonyl oxygen not the hydroxy oxygen. —Preceding unsigned comment added by 137.48.19.23 (talk) 20:57, 17 February 2010 (UTC)

• March supports formation of intermediate 1. German wiki also favors mechanism as presented V8rik (talk) 17:51, 18 February 2010 (UTC)

Wikis aside, carboxylic acids are more likely to be protonated on the carbonyl oxygen; one can then draw resonance structures showing charge delocalization. That said, if there is experimental evidence that the reaction goes via an acylium ion rather than a tetrahedral intermediate, please cite it. —Preceding unsigned comment added by 143.44.131.81 (talk) 17:04, 21 April 2011 (UTC)

• March is not a wiki. March is the book March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure by Jerry March. So take a look in that book. Christian75 (talk) 17:13, 21 April 2011 (UTC)