Tag Archive | azomethine ylides

How did this slip by the referees? Azomethine imines are not azomethine ylides

A recent paper by Xingwei Li and co-workers in Angewandte Chemie International Edition has some nice chemistry in it, but take a look at the title, “Rhodium(III)-catalyzed oxidative C-H functionalization of azomethine ylides.”  One might expect to see some azomethine ylides, right?  No, they are azomethine imines:

I suppose one could make the case that azomethine imines are a subset of azomethine ylides, but I’ve never seen it done.  What am I missing here?

[Edit:  Correspondence with Professor Li reveals his point of view:  “the structure can be called both azomethine ylides and azomethine imines,” (sic) and there “is not much difference,” (I strongly disagree on both counts) and “we simply want to emphasize the ylidic character of our substrate.”  Okay, I can understand wanting to emphasize that something is an ylide, but there’s no need to choose an incorrect name to do so.  Learning organic nomenclature is hard enough.  Enough said.  I’m now going to retire my Professor Pearson hat on this issue.]

[Edit: Here’s another paper from the same lab, still referring to azomethine imines as azomethine ylides.  Apparently the referees at Advanced Synthesis and Catalysis aren’t minding the store either.]

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