As pointed out in the comments to this post, the Menger / Christl pyridinium incident made the mainstream German media in the form of an article in Der Spiegel, which is about as mainstream as it gets. Even a news magazine with a page count as high as that one doesn’t cover organic synthesis very often, so I was curious to see how they handled it. Here’s my own translation of the last part of the article, after Christl sends along the bad news that Menger had rediscovered the century-old Zincke reaction:
Menger reacted reasonably, says Christl. “Fifteen minutes after my e-mail he wrote to me that he would immediately review things”. The American at first believed himself to be in the right: that he really had prepared a new 12-membered ring. “I hate to disappoint you”, wrote Christl, equally sure of himself – and referred to a mass-spectroscopic analysis of the products. These had given a higher molecular mass than a 6-membered ring would. But Menger had overlooked an important detail.
“I am no specialist in analytical methods, but I knew the mass spec method that Menger had employed clusters fragments together", says Christl. During the mass spec analysis, a 6-membered ring could appear to be a 12-membered ring. Menger did not know this effect – “A point we did not realize at the time”, he said remorsefully in the journal Nature. Christl reproaches Menger for imprecise work: “He should have asked a specialist in mass spectroscopy”.
Menger must now send in a correction to his work, and Zincke will be acknowledged. That puts Yamaguchi and Menger hard on Zincke’s trail, says Christl with amusement. Both of them used a particular salt, actually called Zincke salt, in their experiments to prepare the supposed 12-membered rings, but they were obviously completely clueless as to the origin of the name.
But another question remains: How could a 102-year-old reaction simply be overlooked, even though every article in a journal is proofread by an external reviewer?
Zincke had naturally published his work at the time in German. At that time, Germany was a center of research, and English was not yet the official language of science.
But was it really just the language barrier that made the entry into Zincke’s work difficult for Yamaguchi and Menger? Christl says: “This literature is so important, that it’s also given in English”. Maybe not Zincke’s complete original article from the “Annalen”, but at least a description of the reaction in the chemical handbooks. These remain in the libraries.
And here lies the problem, that hardly anyone just looks in the books, complains Cristl. “Young researchers just don’t get up any more from their computers. Most of them don’t even know that such a handbook exists”.
Lack of time and overloading of the reviewers are likely to blame. “They have to proofread a publication, bit by bit, every day. How is that supposed to work?” It seems, over and over, that old reactions are unknowingly rediscovered – because scientists simply don’t do their homework, says Christl. “For well-known scientists, the reading of the literature has become a luxury that they can no longer afford”.
I think we missed a golden opportunity in the penultimate paragraph to learn how to say “young whippersnapper” in German. Applying the term to Fred Menger does require a bit of an imaginative leap, admittedly. I’m glad that Spiegel turned down the chance to make this an “if only people knew German” article, though. But even if Christl’s points about literature searching are valid, I’m not sure that this case illustrates them.
I think this reaction would (should) have been picked up by newfangled tools available to those young ‘uns sitting at their desks. Can you get any more newfangled than Wikipedia? You don't even need SciFinder: a Google search for ("primary amine" pyridinium reaction) will give you this, which should be enough to follow up on. But as for hard-core literature searching, a few minutes of reading the pyridinium + amine literature should have turned up this from 1976 or this from 1970. But why go back that far? How about this review in Angewandte Chemie itself from those far-off days of. . .2006?
No, I don't think the problem here is that people don't know how to turn off the computer and go seek out the good ol' dusty handbook. Those have a lot of good information in them, certainly, and no one's ever cranked out better ones than the Germans have. But the problem here is that people didn't apparently didn't spend any time at all checking the literature. And what's more, the folks who send papers to Angewandte Chemie, and especially the ones who review them, don't even seem to be able to find a key reference published last year in the same damn journal.