I am trying to synthesize poly(ethylene-propylene)amine, i.e.:

enter image description here

I've read that Reductive Amination is efficient regarding the reaction yield. However, it needs aldehydes to start the reaction. To make the aldehydes I can use this way and start from the hydroxyl-terminated polymer compound. I reach to a dilemma here where my experience is not enough to decide which way to go. I can start with a aldehyde-terminated polymer at first so I don't have to make it from an OH-terminated polymer.

Which way do you suggest? A reference on how to do the one you recommend is also appreciated.


Before I offer an answer understand that I am a general synthetic chemist used to working in solution phase, and I have not worked with polymers. Absent an answer from someone who has here is how I would tackle this using OH-terminated polymer.

1 -reaction with methanesulfonyl chloride/triethylamine to activate the -OH for displacement. This is known as mesylation more here and here

2- reaction with sodium azide in DMF or DMSO to give the alkyl azide

3- reduction of the alkyl azide to the amine with triphenyl phosphine Staudinger reduction

|improve this answer|||||

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.