nice simple method

Saw this today in the JOC ASAPs.


I'm a fan of any new method, or method improvement that is simple, efficient, straightforward, and useful. While I haven't ever made a sulfonamide that wasn't a protecting group, they are handy for other things, and pop up in drugs as well. These guys got the reaction to work with one set of conditions on electron rich and poor aromatic thiols, a few aliphatic as well, and it appears to be selective and mild as well.

In fact the only things I can negatively comment on at all are that I would have liked to see more aliphatic examples, and acetonitrile is an expensive solvent. However, I bet that within the next year or so people will be buying cars in stupid numbers again, and acetonitrile will come back down in price.

Edit: I somehow gave the wrong journal title, but the right link. Thanks to Dr. Miller for pointing it out.

great idea

Yesterday our lab and another had the privilege to go have lunch with Philip S. Portoghese and see him give a seminar later. During lunch we were talking about journals and the state of the business of journals, he's been the editor of J. Med. Chem. for 37 years, and ACS's new headache inducing paper journal format where they have two pages of material per page of paper came up. I mentioned that it felt like I was reading a girlie magazine whenever I turned it sideways to flip through the issue, and someone else in attendance remarked that we should have a centerfold with a reaction or compound of the month. What an awesome idea! People would be vying for the cover with pretty pictures, but others would be competing to get the centerfold with great science! Truly an idea who's time has come!

edit:
I said something stupid, and would like to clarify. You usually get the cover by publishing good work, but the cover itself is something pretty that is related to the work, and usually not the work itself.

The centerfold could be pure, unadulterated, awesome science.

Somebody Explain

Am I missing something?



This is a really expensive and complicated way to do a sophomore organic reaction. Instead of making the silyl enol ether and treating it with stoichiometric CAN and 2,6-di-tBuPy (both expensive and used in large excess 2 eq and 4 eq respectively), why not just deprotonate with LDA and add an allyl halide?

Can anyone think of a reason to do this reaction (aside from somehow publishing it in Org Lett)?

ignorance is bliss

Our secretary is a true sweetheart, but is also rather fond of drama, especially if it is totally unnecessary. A recent example includes someone attributing her name to a work order incorrectly. This would usually involve a simple "that wasn't me" phone call or email to rectify, but for her she planned out an involved strategy of who needs to be contacted and provisions for difficulty with backup plans. In reality the order actually has nothing to do with her at all, excepting the bookkeeping error, and she could simply ignore the problem and it would go away.

Typically when I talk to her, like after a morning greeting, I'm prepared for some sort of soliloquy on her crushing life events. I try to remain stoic throughout. She's a sweetie, so I don't want to shut her down, but I also don't want to add fuel to the fire. Typically I give her some noncommittal remarks, and, if I actually have any knowledge of the area, some help.

Today she was extra excited and proceeded to tell me a story about a man who had some rare condition and had kept a gorilla in his basement and fought with it for several years until it had actually killed him, even tearing off his arm at one point. I, politely, called bullshit, and recommended she check it on snopes.com. She continued like she hadn't heard anything so I nodded, repeated myself, she continued, I spelled snopes.com for her, and then left. A little while later she said she had found the article and tried to give it to me, so I chatted with her, but didn't take the article and left.

Eventually I had a minute and was curious so I actually looked it up using some nice generic, but defining terms, and it popped right up as hit number one. As it turns out it's an onion article, and her lack of understanding was so goddamned hilarious I couldn't decide whether to tell her or not. In the end I told her. There was no practical way to follow the progress of the story as she told it to other people, so the entertainment value was pretty much used up, and it was time for some modicum of damage control.

wow

It's hard to say if this is completely and utterly awesome, or just another interesting blip on the radar that may someday make it into textbooks.

JACS ASAP, DOI: 10.1021/ja9061097

I had and organic prof. years ago who referred to fullerenes as full of shit arenes, due to all the press they had garnered with little real applications found. They still have produced relatively little, especially when compared to sibling compounds such as carbon nanotubes, but every now and then something really neat like this comes out.


Also I learned a new word today, that I wish I hadn't: Suicidality.

practicality

This went to ASAP a little while ago. The method is interesting, and apparently successful, but the thing I liked most about it was one of the footnotes.


It's a bit unfortunate that a good method needs to be supported for not being catalytic, or any other little darling of the day, but it's nice to see it done once in a while.

It seems like most people who use buzzwords, especially in the title of the article, really do the buzzword in question a disservice, and it has little to do with the method besides poor advertising.

fun weekend

Esther came to town for a visit this last weekend, and we got to do some fun stuff. In addition to the fun stuff we ran into some interesting and odd things too, two of which I thought I would share.

On Saturday we thought we would go to Old Town Alexandria and check out the Torpedo Factory. We'd never been and heard it was neat, if the chance arises to go there, I recommend it. that place was pretty damn cool.

On the way out of town to go there we knew it was going to be a long day, so we stopped off at the CVS to get some water bottles to take. And the expected customers for a Saturday morning were milling around the store. Only one thing stood out, and I wouldn't have noticed it at all if I hadn't happened to look over at just the right time. There was a little old lady browsing in an aisle who looked for all the world like any middle America grandmother except for one thing. She had no nose. Where her nose had once, presumably, been was a flat spot covered by a triangular band-aid. For just a moment I involuntarily thought of Vincent D'Onofrio's character Pooh-Bear from the Salton Sea, and subsequently of his pet/torture device badger Captain Stubing. Rather an odd juxtaposition for a nameless granny.

I couldn't find a pic of him without the bad prosthesis, sorry

The other encounter happened when we went to a movie one night. We saw District 9, and pretty early on I had to go to the bathroom, and I felt it would be best to get it out of the way before all the crazy action really started in earnest. It just so happened that there was a unisex singlr bathroom right outside our theater that was open. As I approached it, I could see through the slightly open door that someone had already vomited in there. I peeked my head in to see how bad it was, to determine if I could still use it, or would need to look for another. I was shocked to see that not only had someone basically turned their entire alimentary canal inside out, but they had placed the bulk of the detritus as far from the toilet and trash can as possible while still residing in the same room.



In addition to the grotesque landscape was a not unpleasant odor of blueberries or raspberries. So I was able to use the bathroom in relative comfort, even in that state. I went back after the movie to snap these pics and the odor had persisted.