# What are the products of alkene oxymercuration with diols?

I was wondering what would be the product of the reaction of alkene with a diol (such as glycol) in alkoxymerucuration/demercuration, i.e. $$\ce{(CF3CO2)2Hg/NaBH4}$$?

I tried to look online but I couldn't land on a paper or website that goes through such reaction. I also tried Scifinder, I marked both compounds as reactants, but zero results stemmed from the reactants! Any input?

I'm thinking if these possibilities (I have more possibilities in my mind, but for example I selected three) are structurally accurate and energetically stable to be produced in such reaction and which is favored?

To classify them more ... to single and di addition, here is what I'm thinking:

• Oxymercuration is often run in the presence of excess water or alcohol, but only one RO/OH adds. Therefore I presume in the presence of a diol you get mono-addition by one of the 2 available OHs, probably the least hindered. en.wikipedia.org/wiki/Oxymercuration_reaction Nov 8 '20 at 8:32
• @Mithoron so Alkoxymercuration/demercuration (CF3CO2)2Hg/NaBH4) won't force this reaction? if it doesn't what can force this reaction? I want to see whether such reaction will add seperate glycol on each carbon of the double bond, or the glycol will form a cyclic with the two carbon of the double bonds?
– user99277
Nov 8 '20 at 17:21
• I think the top left option is most likely. I see no reason why you would get di-addition to the alkene Nov 8 '20 at 19:11
• @Waylander I updated the question with single and di-addition possibilities, I'm not sure if excess of glycol or other factors will move the reaction toward single or di-addition or toward open or cyclic formation in either case.
– user99277
Nov 8 '20 at 20:10
• In your original scheme, the product in the upper left would likely have the hydroxyl attach to the benzylic position. Two of the remaining three products involve C-C bond formation. How is that accomplished with oxymercuration? Nov 8 '20 at 20:11