There’s a rather embarrassing note leading off the latest issue of Angewandte Chemie. Two recent papers (2007, 2006) had reported the synthesis of some rather weird 12—membered rings, the diazaannulenes shown here. They made them from dinitrophenyl pyridium salts and primary amines, with the pyridine ring unraveling oddly along the way. Too oddly.
Professor Manfred Cristl of Wurzburg, who apparently knows his pyridinium chemistry pretty well, recognized this as an old way to make further pyridinium salts, not funky twelve-membered rings. He recounts how over the last couple of months he exchanged awkward e-mails with the two sets of authors, pointing out that they seem to have rediscovered a 100-year-old reaction, and have they really looked at their spectral data closely, eh? Both groups have admitted their mistake – the data match up wonderfully with the known pyridinium compounds, unfortunately, so there’s really no other way out – and retractions are appearing.
He raises some broader points, though: first, there’s the obvious problem that this whole thing should have been caught by better literature searching and analytical chemistry. These arresting structures deserved more than a quick NMR and LC/MS, and they deserved more than what appears to have been a not-very-thorough look through the prior art. There’s a bigger problem, though, which fans of the LaClair imbroglio will enjoy. Note the exasperated tone of the following, which comes across in a very German fashion:
”A further question refers to the reviewing of the above papers. Presumably, at least four referees were entrusted with this duty, two of Angewandte Chemie and two of Organic Letters. They have provided conclusive evidence for their lack of knowledge of heterocyclic chemistry. However, the referees are probably chosen by the editorial offices according to the specialization of the corresponding authors and, thus, have the same gaps in the knowledge as the authors. In consequence, if the authors present results remote of their main projects, extreme misjudgments are inevitable. . .”
So, once again, Angewandte Chemie's reputation is upended by sloppy refereeing and editing. This time, though, they run an article berating themselves. Progress, I'd say. . .
(Note: update on this story here, and why it might have happened, here).