Lamentations on Chemistry

A little Cabernet Sauvignon, Blue Man Group, some Gilbert & Sullivan- life is good. I nearly forgot I have to go to work in the morning. Dash it all, damn and blast.

Our IT guy has been hounding us to make better choices for login passwords into the company information system. More characters, digits, and the use of mixed case is recommended. Like many people, I have accounts in diverse systems that are not connected. Not every system gives me a choice of login names and passwords.  Eventually one ends up with a variety of codewords that one has to keep straight. Soon it becomes a little burdensome.

There is a website that purports to provide random character strings. It is Random.org.  The operator of the site is a lecturer in computer science at Trinity College and uses atmospheric noise from a group of radios to capture random events that are somehow translated into character strings.

If you need strings of random digits, there is von Neumann’s middle square method. It can be done on a calculator. While it is hard to guarantee that there isn’t some kind of periodicity, von Neumann felt this method suited his needs.

I wonder to what extent the shaky state of internet security depends on the structure and prevalence of Microsoft code?  I have no idea.

Larry, Moe, and Curly.  Or some Rogers and Hammerstein musical horribly miscast.

The literature train station is overflowing with diverse catalysts for the large variety of coupling reactions out there, as is the patent literature. Parties scramble to get window seats on the IP Express, the high speed non-stop to that Golden City on the Hill. 

A recent JOC article disclosing an inexpensive catalyst system that struck me as interesting.  The article by Guo and Liu emphasizes economy and so discloses a phosphorus-free bidentate ligand system that affords Heck and Suzuki-type coupled products.  There are pluses and minuses to this system, as is the case for most catalysts.

On the plus side with the Heck and Suzuki reactions, both activated and deactivated aryls gave decent yields. On the minus side, the Heck coupling reaction is a bit slow. A fair amount of energy input was needed- 130 C in DMF over 30 hours. On the Suzuki side, most reported reactions resulted in good yields, except for the aryl chlorides. The relative inertness of chlorides is not particularly unusual, but it may cause this catalyst to be passed over in some applications where the less atom-efficient bromides and iodides have been targeted for replacement.

Finally, the apparent requirement of DMF is rarely happy news. Regardless, I have no doubt that this catalyst will find its way into the future literature and many clever applications will be revealed.  As of this writing, I was unable to find a US patent by inventors Guo and Liu claiming this technology. Since there is a 1 year limit on the filing of a patent application following disclosure, this technology could be in patent prosecution at present. Or not. Wouldn’t it be a happy thing for it to be in the public domain?