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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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In the Pipeline

« Some Perspective | Main | More on Woodward »

November 29, 2004

Archaeologists Announce Dirty Laundry Discovery

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Posted by Derek

Hey, brain researchers! Want to unravel the fine details of long-term memory? Looking for the longest of long-term potentiations? Just go out and rope in a few scientists. No, not to do the research - to do the research on. If you can find some that feel that they've been cut out of the credit for a discovery, you've got the best subjects you could ever want.

Consider some research that look place in the mid-1960s at Harvard. R.B. Woodward was Harvard's star organic chemist, a man whose name is still used as a shorthand for extraordinary talent. His work with Albert Eschenmoser to synthesize Vitamin B12 is considered one of the great syntheses of all time, and it was a set of problems in that project that set him to working with theoretician Roald Hoffmann to codify what was going on. Chemists everywhere are now familiar with the Woodward-Hoffmann rules for pericyclic reactions, which tied a whole list of cyclizations and rearrangements into a coherent bundle. Hoffmann and his collaborator Kenichi Fukui won the 1981 Nobel prize, and if Woodward had been alive he very likely would have joined them to win his (nearly unheard-of) second one.

Enter E. J. Corey, who took over the position of mighty synthetic powerhouse at Harvard after Woodward's death and won a Nobel of his own in 1990. In his acceptance speech earlier this year for the American Chemical Society's Priestly Medal, Corey mentioned the Woodward-Hoffman work, and mentioned in passing that he had actually put Woodward onto the path that led to the correct solution. This was news to just about everyone - well, except for a few people Corey had complained to over the years, not least of them Roald Hoffmann himself.

Now Hoffmann has replied, in a highly unusual five-page letter in Angewandte Chemie. (Those links may not work for nonsubscribers - try this roundup from Nature instead.) He goes into a lot more detail than Corey's spoken claim did, feeling (correctly, I'd say) that the gloves are now off. As it turns out, Corey wrote a letter to Hoffmann in 1981 giving his account of his conversation with Woodward, and describes how the next day he heard Woodward refer to the idea as his:

"In a manner of which few would be capable he pirated the idea, evidently preferring that over my good will. Even more incredible than what Bob did was how he did it. . ."

Thus said Corey, and he attached a plea that Hoffmann set the record straight in his Nobel acceptance speech. This chance Hoffman declined, as anyone would have guessed, since Bob Woodward had been dead for two years and the only person who could attest to the conversation was Corey himself. A follow-up letter from Corey was full of unretractable fighting words. Hoffmann mentions that he went on to meet with Corey personally in 1984, but how he managed to make himself do that after this sort of stuff is beyond me:

"You cannot deny that despite the possibility of appalling dishonesty at the roots of your collaboration with Bob, you elected to close your mind. . .please consider that history many not deal leniently in this matter, taking seriously the possibility not only of Bob's dishonesty, but of your own not unwitting participation in the extension of fraud."

Hoffmann goes into great detail on his side of the 1964 story, and he has some good evidence that Woodward was already on the track of the idea that Corey claims to have suggested to him. (He also reports that Woodward denied to him that Corey was a contributor to the work, but that's another conversation we have only one side of.) But Hoffmann also gets in a kidney punch, showing that Corey published a paper the next year that would have been an ideal showcase for his understanding of the relevant concepts, but said nothing about them.

Corey never went public with his claim until this year, although it seems that for years he's vented to a number of prominent chemists and fellow Harvard faculty members. It's clearly been eating away at him all this time, and for some reason - intimations of mortality? - he feels that it's time to haul out this ancient dispute.

I never met Woodward - first-year undergraduates in Arkansas didn't cross his path much - but I've met (casually) both Corey and Hoffman, and I've worked with students and post-docs of all three of them. Overall, I'd say I believe Hoffmann here. Although I think that Corey probably did have what he saw as a key conversation with Woodward in May of 1964, I'm not so sure that Woodward saw it as such a turning point. There's no way for us to know - even if Woodward had lived to comment, I doubt if that would have cleared things up any more. (Of course, Corey had fifteen years to speak up while Woodward was alive, a point Hoffmann misses no opportunities to make.)

What I'm sure of, though, is that Corey is doing himself no good at all. Chemists all over the world are saying to themselves "This guy has a Nobel already, what else does he want?" One problem is that some of this springs from the same qualities that got Corey to where he is. The persistence that's kept this simmering in him from 1964 to 2004 is the same persistence that's taken him through a huge array of impressively difficult molecules. But this is all a useless wound to his own reputation. There are, after all, more important things than being right.

Comments (4) + TrackBacks (0) | Category: Chemical News


COMMENTS

1. The Novice Chemist on November 30, 2004 8:06 PM writes...

A side question: why is it that Angewandte attracts the papers that it does? In other words, why didn't Hoffman send this paper to JACS instead?

I can never figure out why some papers are in Angewandte and others are in JACS; it almost seems like there's some 'journal pecking order' that I'm not getting. Anyone have an idea?

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2. Derek Lowe on November 30, 2004 8:16 PM writes...

Well, there's certainly a pecking order, but I don't know if it's fine enough to distinguish between two top-of-the-heap journals like JACS and Angewandte. But the latter is where the classic Woodward-Hoffman overview paper appeared, way back when, complete with (then-unusual) color printing of the molecular orbitals. So Hoffmann has, I think, an affinity for it. Angewandte also publishes more personal and historical articles, which JACS has never really had an interest in.

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3. Drew on November 30, 2004 11:06 PM writes...


Actually, he likely should have gotten *three* Nobels, including ferrocene, although that was pretty contentious back in the day...

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4. SRC on November 30, 2004 11:08 PM writes...

Angewandte Chemie's rise to prominence is relatively recent (i.e., in the last 15 or so years), and is largely attributable to the editor who took charge then (whose name escapes me at the moment).

Back when the Woodward-Hoffman rules were published, Angewandte Chemie was much more obscure than it is today. OTOH, Woodward spent much of his time in Switzerland (certainly in his later years - not sure about then), which may have influenced the choice of journal (Roald Hoffman was then a grad student, and presumably had little say).

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