Sciencemadness Discussion Board

Cyclopentadiene

Triflic Acid - 13-1-2021 at 22:32

I can buy ferrocene from eBay, and I think that acidifying it would give me cyclopentadiene. Distilling the acidic mixture should give me pure cyclopentadiene. Would this work? I want cyclopentadiene to make other metallocenes by turning the cyclopentadiene into sodium cyclopentadiene-ide and reacting that with anhydrous metal chlorides in Et2O. The anhydrous metal chlorides are made by bubbling anhydrous HCl or Cl2 gas through a metal in MeOH.

DraconicAcid - 13-1-2021 at 22:41

I don't think ferrocene is easily decomposed with acid.

BromicAcid - 2-2-2022 at 14:56

Found this post at work while looking up some things on decomposing ferrocene. Strong acids can make the ferrocenium cation. Seems like it's usually made (or at least sold/isolated) as the tetrafluoroborate salt but I did see an aqueous workup for a lab prep on ferrocene where as part of the workup they treated the reaction mixture with hydrochloric acid and in the notes it said that the blue filtrate was from ferrocenium. When I was trying to think of something to possibly complex with the iron strongly enough to kick off that cyclopentadiene I did wonder about oxalic acid. Interestingly enough there are papers out there where people have gone just that route which does result in a much lower decomposition temperature vs that of neat ferrocene but I didn't dig into what products were formed.

Triflic Acid - 3-6-2022 at 21:25

Interesting. Just came across this randomly. I gave up on the project and moved on, but I might just try this someday. Seems interesting enough.