A Pale Blue Gas: Part 2

The product of the reaction was a radical, traditionally an unstable, reactive family of compounds with only a fleeting existence. In this case the heterocycle was stabilized by extensive pi delocalization and the carbon atoms were shielded and electronically changed by attachment to electronegative, kinetically stable CF3 groups. This also meant that the melting point of 12 degrees C resulted in a liquid with a significant vapour pressure at room temperature. This resulted in the blue gas.
I remember when I did the melting point. I had laboriously prepared the cation salt and reduced with huge excess of sodium dithionite and then fractionally distilled the volatile products three times to remove solvent and bi-products (which I would discover later to be the result of facile photolysis reactions). Then when I had grams of pure dark green black liquid I froze it and slowly warmed the solid in a Dewar until I reached the melting point. What i was not ready for was the high volatility of the solid near its melting point and soon I had huge shiny blue-black crystals growing perpendicular from the side of the flask. They were altogether some of the most beautiful things that I had ever seen. I would spend a whole year of my life preparing and characterizing this compound. The last problem to fall was the precipitation of the photolytic impurities using a method I had stumbled across in a 1908 JACS paper written by Speed Marvel in which he noted that he had precipitated polysulphide impurities with a catalytic addition of amine. I found a whisper of triethyl amine did the trick just fine.

I had pretty much photolysed the last best sample that I had in a heroic attempt to determine the vapour pressure of the liquid and solid when the word came down from Jack that a picture of the blue gas was needed the next day for an important conference in Europe. In one day I pushed a new preparation through and did the reduction and fractional distillation of the bits and scraps of material that I had available. In the meantime I took a virgin Pyrex flask and attached a new rotoflow tap and sealed off the neck to make a collection tube. I knew that the very process of placing the carefully prepared liquid in the flask and exposing it to light would destroy the compound but it needed to be done. The sample prepared the photographer was a somewhat eccentric natural light purist and he insisted that on a cold day we take the flask outside. I kept the flask warm inside my shirt with the sample tube exposed so that the liquid would remain in the tube and the flask would be filled with the blue gas. Then when the photographer said he was ready I whipped the flask out, clamped it and the picture was taken. If you look closely you can see two things. The neck connecting the valve to the flask got cold quickly and the liquid started to condense and there is a reflection of the UNB Biology Building on the surface of the flask. Thus the only picture of the blue gas was done. There would be no more.