I am in a bit of a pickle with my friend oxetane. I do not want it to open up, but it keeps on doing things I do not want it to do such as open up, polymerize etc. I have been gentle, careful and followed the procedures that are known to keep it intact. The story is, initially, I had a synthetic route where I had acid labile protecting groups, but, using acid opened up the ring. I used HCl and I know it is harsh but the acid labile groups were being resilient. Next, I planned a new route using base labile groups. Oxetane mainly behaves, but another part of the molecule does not behave well at all and does all sorts of rearrangements. So there is no way I can go this route with base labile protecting groups. I am more confident that I can handle the oxetane sensitivity to acid over the other part which is base labile (can not reveal entity unfortunately due to IP issues).
So, to ask a simple question, if you HAD to use an acid to remove let us say tert-butyl group or a boc without the oxetane opening up which condition would you use/recommend?
Thanks in advance,