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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: Twitter: Dereklowe

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March 4, 2013

The IBX Answer

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Posted by Derek

I wanted to point out what looks like the resolution of the Blog Syn story about IBX oxidations. See Arr Oh seems to have discovered the discrepancy that's been kicking the results around all over the place: water in the IBX itself. So it looks like this whole effort has ended up discovering something important that we didn't know about the reaction, and nailed down yet another variable. Congratulations!

Comments (9) + TrackBacks (0) | Category: Chemical News


1. newnickname on March 4, 2013 12:46 PM writes...

I think it came up in an earlier part of the IBX series of Pipeline discussions that Schreiber group had shown that water was crucial with Dess-Martin: S. D. Meyer, S. L. Schreiber, J. Org. Chem., 1994, 59, 7549-7552.

A reply to this comment at Blog Syn about publishing the results: "By the way, do peer-review journals explicitly prohibit anonymous submissions?" The defunct ACS journal CHEMTECH published at least one paper under a pseudonym to protect the author against possible retaliation from employers. It might not have been peer-reviewed, but it was checked. The founders-editors of CHEMTECH (Luberoff, et al) were pretty good that way.

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2. yoyomama on March 4, 2013 1:21 PM writes...

I don't think that anonymity is necessarily a bad thing in the greater scheme of things. In a tough job market, no one really knows what sort of social media behavior will be the straw that breaks the camel's back in the hiring process. I have seen some unlikely straws in reference letters do the trick so who knows what blogosphere, facebook, instagram or twitter infractions will do likewise.

I remember well on Paul Bracher's blog during a discussion of a now not so recent academic hiring, an academic commented about what that particular post might do to his future job prospects. Paul being his own webmaster was able to figure out which university the comment came from, but it raised an important point about social media and its possible future career ramifications.

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3. milkshake on March 4, 2013 2:39 PM writes...

looks like after some teeth gnashing, Baran group just started a new blog last week:

openflask.blogspot (com)

If you can't defeat them, join them

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4. dave w on March 4, 2013 3:16 PM writes...

This is a little unusual, isn't it? I thought
the usual issue with traces of water in organic
reactions was that they mess up the desired process,
rather than facilitating it!

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5. bcpmoon on March 5, 2013 1:28 AM writes...

Par for the course for Process chemists, I might add. It regularly happens that a synthesis does not work on scale because the starting materials are uncontaminated in bulk (although most of the time the problem is the opposite). And as inertization is much better in a plant, lack of oxygen and/or water can doom a reaction.

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6. Anonymous on March 5, 2013 7:26 AM writes...

It's customary in the university environment to scrupulously dry everything, glassware baked at 150°C overnight, stills (or drying systems nowadays) for all solvents, but once in industry, nobody bothers as it's mostly unnecessary. It's simply the first port of call of any questioner in meetings when a reaction hasn't worked as well as expected (Did you massively dry everything? How? Aahhh, that'll be why then!) without anyone really believing that's the cause.
Lithium-halogen exchange and the like on 50mg, yeah, you need dry THF.
Anything else, no need.

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7. Sam Adams The Dog on March 5, 2013 7:52 AM writes...

Then there's the apocryphal story about the company who set up a spy as a janitor to figure out how come the night shift always got a higher yield. He discovered that at 3 AM, the foreman stood on the catwalk and peed in the vat....

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8. Rhen on March 5, 2013 11:29 AM writes...

@dave w, I think there were other instances where water plays an important role in a reaction. The one I'm thinking right now is the Et3B/air/H2O deoxygenation condition from John Wood. And this is not counting all the "on-water" reactions out there...

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9. Andrew (@_byronmiller) on March 5, 2013 12:37 PM writes...

@Rhen - or hydrolysis? (I'm sorry. I'll return my degree now.)

@yoyomama - I think that is a very good reason for the BlogSyn folk to remain pseudonymous (there's a nice discussion of this in the comments here: That said, I can see why people who aren't habitually participating in the online community are very skeptical of pseudonymous critics - who are these guys, anyway?!

It'll be interesting to see how this plays out long-run, especially if they keep turning up useful info on small effects like this.

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