jenijjun - 21-7-2021 at 02:10
I was thinking about using IBX to selectively oxidize primary alcohols to aldehydes.
I've found papers using various solvents like acetone/water mixture[1], 2-methyl-2-propanol[2], DMSO or bromobenzene[3].
If someone had access to this paper[4] that would be great, it talks about easy oxidation and reusing the oxidant.
My question is:
1) What would be in general the best solvent & How to choose the most suitable solvent for a reaction?
2) Is this workup procedure correct?
"IBX reduces to iodosobenzoic acid which can be filtered out together with leftover IBX and oxidized back to IBX using Oxone and reused. After
filtering the reaction mixture and distilling the solvent, we get reasonably pure aldehyde for further use."
3) Could be IBX prepared in situ from 2-iodobenzoic acid and potassium persulfate?
refs:
[1] https://pubs.acs.org/doi/abs/10.1021/jo026751w
[2] https://www.sciencedirect.com/science/article/abs/pii/S00404...
[3] https://www.scripps.edu/baran/images/pdf/pdf29.pdf
[4] https://pubs.acs.org/doi/10.1021/ol026427n
[Edited on 21-7-2021 by jenijjun]
karlos³ - 21-7-2021 at 03:44
Here is the paper you requested.
Attachment: more2002.pdf (52kB)
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jenijjun - 22-7-2021 at 01:08
Thanks, that was helpful. And does anyone have access to this one? It deals with regeneration of IBX in situ.
https://pubs.rsc.org/en/content/articlelanding/2016/nj/c6nj0...
karlos³ - 22-7-2021 at 01:45
Its attached.
It seems like you don't know sci-hub(.do) yet?
You can fetch any document with its DOI by copying it in, everything up until 2020 though, nothing that comes later.
Attachment: bikshapathi2016.pdf (724kB)
This file has been downloaded 227 times
jenijjun - 22-7-2021 at 02:41
Oh I didn't know that, thanks for your help
I'll definitely use that