njl - 19-1-2021 at 08:04
I found the following paper that details a huge number of organic reactions, many of which I had never seen before. It includes the reaction,
variations, mechanisms, and examples of the reactions application. I hope you find it as interesting as I did.
https://sci-hub.st/https://doi.org/10.1002%2F9780471739876
I'm not sure if this is already in the library but if not it might be worthy.
njl - 19-1-2021 at 09:30
Particularly interesting to me is the Quelet reaction, as well as Prins reaction and glycol synthesis using I2 and a silver carboxylate. The
intermediate iodinium/acetal looks interesting since the stabilized carbocation between the 2 oxygens looks like it could be easily alkylated,
followed by hydrolysis to give a ketone.
chemist1243 - 12-3-2021 at 11:53
you have really stumbled upon something! This is just awesome. I really hope they add this to the library if it isnt already there.
Where is the glycol synthesis using I2 and silver carboxylate? That looks pretty interesting. There’s so much to unpack still, I can see some real
gems coming out of this if one went deep enough into.
njl - 12-3-2021 at 14:05
There's 2, Woodward hydroxylation gives cis diols while the Prevost reaction gives trans diols. The difference is mainly in the steric bulk of the
carboxylic acid. Typically in the Woodward Ag acetate is used, which facilitates the cis-product formation since acetate is rather small. The Prevost
uses Ag benzoate, which is too big to give cis-products (the intermediate diester can't have both carboxylate groups on the same side of the bond).