[Jetsam]

Hello. Can you look at my mechanic reaction of isopulegon from citronellol?
I dont know how to write a proton transfer and i dont know the rest is correct

[rolnor]

There seems to be a lot of pages on the web that describes the synthesis.


https://www.researchgate.net/figure/Mechanism-of-Citronellal-Cyclization-Tursiloadi-et-al-2015_fig5_353602161

[romitvo1]

I'm having a hard time understanding this alcohol oxidation. I know that adding PCC to the primary alcohol will produce an aldehyde, but I'm not sure how it becomes cyclic. I originally thought that it was the OCOCH3-, but the formation of isopulegone from PCC alone has me confused.

I tried to guess at the structure for A based on the mass and peak at 1730, but I'm pretty sure it is incorrect. Could someone explain how the citronellol becomes cyclic after PCC and what the role of the OCOCH3- is for A?

Also, for the addition of OH- to isopulegone, I thought it was that the OH- attacks the carbonyl C, but I get a geminal diol and am not sure how to proceed from there.