[kamiyu]

I strongly feel that this forum is an excellent platform for sharing our unusual experiences of lab work. I think we should share those in this forum so that we can all learn from each other

I am working on synthesizing novel optoelectronic materials such as OLED and OPV materials. The striking features of this on contrary to that of traditional medicinal organic chemistry is the involvement of many phenyl rings and lack of chiral centers.
One of my experiences is about TLC/chromatography.

For one reactions that I struggled several months ago, the TLC of my product after column is a wide band irrespective of concentration. The NMR shows not pure and I could judge from the NMR there are three components. In this case I added a bit triethylamine to the mobile phase, and three spots showed up. I think triethylamine helps a lot when it comes to puzzled TLC or column.

[kriggy]

I had similar problem, I added amine but it didnt work wery well for me.
Anyway I will share my small experience:
While doing my thesis, I found out that amide like this

cant be reduced to amine by LiAlH₄. After short literature search I found out that those kind of coumpouds cant be reduced by BH₃, LiAlH₄ or other agents.
Whats even more interesting (for me) is that amide reduction by LiAlH₄ is reaction I find in almost every book but it somehow doesnt work with this compound (or similar ones).

[kamiyu]

Thanks for your sharing.

I remember one big organic synthetic guy (should be Robert Burn Woodwards) once said that every reaction was a new one. You never know if it works or not till you try it out.

I was once told one guy failed his total synthesis for a step which is very trivial that it should work, but it never. It ended up wasting TWO YEARS' time.

What a pity!