bloodline wrote:
@karlos
Hahahaha! yeah, organic chemistry was never my fortè either :-D
Yes, but it was mine :lol: The stuff I was doing at the time however, was entirely novel and was based on my bosses earlier research into (chirally) directed metallation by rotationally restricted amides. Great stuff, except removing the amide (in it's entirety) is next to bloody impossible without destroying whatever else you have in your substrate.
My task was to investigate using removable sulfone / sulfonamide derived systems instead of the above amides, since cleaving these off later is not particulalry difficult.
The first step was to prepare them and investigate their low temperature properties (to see if the sulfur based replacement for the amide sterically locks out and stops rotating). This alone took a few months :-/
Due to the size differences and bond angle issues, getting such a rotationally inhibited sulfonamide was not entirely straightforward. Having to wait weeks at a time for a set of low temperature NMR (getting the spectra for the same sample from say -80C to room temp in 5C increments) didn't exactly help.
Unfortunately, just as I was starting to get somewhere, those neer-do-well Japanese industrial chemists jumped in and published work they'd been secretivley working on, rendering all my work useless. Absolutely nobody awards a PhD for second place.
By then I was pretty disillusioned to say the least...
