Old Procedures

What follows is a collection of thoughts that I’ve had over the past few days….

There is something about old literature (back in the golden days of organic when you could do pretty much anything and get decent funding, back when physical organic was big etc.) that was lost on me until recently. So I mentioned in my post about the tropylium article that I actually wanted to pursue it. Well, I did. Sorta. I spent part of Monday just making the salt. I gather chemicals probably from half the labs at UConn to make it but sure enough there I was dissolving triphenylcarbinol in acetic anhydride. Let me tell you, it was by far the coolest reaction I’ve done. To date. I treated my anhydride-carbinol solution (which needed heating to dissolve all the carbinol) with tetrafluoroboric acid (or fluorous boric acid). It instantaneously…like with one drop… turned neon yellow. Then it proceeded to turn red, like setting sun red. It was quite an amazing sight. Then, I added cycloheptatriene. Now mechanistically what happens next is awesome. A through-space hydride transfer. Whether that’s really the case or some sort of electrophilc addition/weird rearrangement is up for debate. Regardless as soon as I finished adding it, you could see what looked like salt appear in the solution. Now what I just described is exactly what the procedure described. Like I did it as they outlined and it worked. That’s how chemistry should be written, so any idiot can go into a lab and do it (with some basic chemical knowledge). I think this generation of chemistry (with fancy catalysts and high EE etc) has lost that. I mean there are exceptions, but I feel people focus less on simplicity and more on yields DR etc. Honest, if it sounds too complicated or impractical, I’m not going to do it. It’s not worth the frustration or my time. And that’s the thing I really respect about old literature. It was simple but effective. It was driven by curiosity rather than grant money. Call me an idealist but if you look at all the chemical knowledge that’s been assembled, how often was it that the project that someone set out to do was the one they ended up doing. Not often. Science is about discovering the unknown. True, some discoveries are far more important than others. But I feel that it should ultimately be about the expansion of knowledge, rather than directed learning.
That leads me to a counter point. The old generation of chemist….they had it easy in some ways. Of course they didn’t have our fancy equipment and computers to do a lot of the analysis for them. But what they did have is an open field to explore, not only in terms of grant money but in terms of the actually chemical world. Reactions like Suzuki coupling (which many of us take for granted now) or even common techniques like flash column chromatography were still out there ripe for the picking. Plus journals were a lot more lenient in what they would accept. Of course the peer review process was definitely operation and work had to be evidenced. But still, I feel that they had such a range of topics to look at that the modern organic chemist (myself) is stuck scraping the bottom of the barrel…or maybe that basic idea just hasn’t hit me yet 😛

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1 Comment

  1. […] the hardest aspect of any graduate student’s career mostly because of my discussion in an earlier post. Plus you feel a sense of complacence because you are kind of owning science (or at least you think […]


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