Tuesday, April 24, 2007

Wiki Paper Experiment Started

Although we still have a few loose ends to tie up, I started writing up our work on the Ugi reaction on the wiki. So far I have abstract up.

Anatomy of the Ugi Reaction and Attempted Cyclization to Diketopiperazines

Reaction profiling using H NMR spectroscopy was used to elucidate the kinetics and progression of the 4-component Ugi reaction, involving an aldehyde, an amine, a carboxylic acid and an isonitrile. Aromatic aldehydes such as benzaldehyde, veratraldehyde and piperonal were found to react smoothly with 5-methylfurfurylamine and t-butylamine to yield imines in methanol. Phenylacetaldehyde led to intractable (product mixtures within minutes of adding to the amine component. The addition of boc-gly alone led to a reversal of the imine formation, while the addition of boc-gly with t-butyl isonitrile or benzyl isonitrile led to a more limited reversal to the aldehyde that peaked after about 30 min before diminishing again over several days. The Ugi products started to crystallize within hours or days. 2-morpholinoethyl isonitrile did not generate Ugi products, apparently due to its instability in the presence of boc-gly.

The experiment will consist in seeing which chemistry publishers will accept a paper written on a public wiki and the use of links to experiment pages on a laboratory notebook wiki as valid references. As I learned from a talk by one our librarians Jane Bryan a few weeks ago, publishers are really becoming tolerant of pre-prints hosted on institutional repositories. This is really not that different.

Who knows - it might even work for an ACS journal. We'll see.

And in the meantime, feedback is welcome on the drafts.

(Note that Alicia also started writing her Masters Thesis on the wiki.)


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