Hi all, Here is the problem:
I am doing an N-alkylation of a secondary amine with triphenylmethylbromide. When I monitored the progress by TLC. I observed many different spots (around 6 major spots, some minor spots are hard to observe).(which I expected only 2 spots should be observed, "MONO" and "BIS" N-alkylation since there are 2 identical secondary amine on the molecule )
I wonder if the other spots on the TLC are due to triphenylmethyl cation rearrangement? Like the image below:
![](https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fimg171.imageshack.us%2Fimg171%2F5831%2Fdsc2346k.jpg&hash=9c864165a51ed1b6ecf496ae99793969efd303af)
Should I expect the tertiary triphenylmethyl cation to rearrange itself to a less stable secondary cation?
I carried out the reaction at room condition, and I am trying to do it again later at lower temp. and one at a higher reflux temp.