An inorganic question - Ions!

[clubcard]

I am just trying to recall a paper I read many years ago. It concerned swapping an N-substitution of a tertiary amine via a 2-step route in which a quaternary salt was formed e.g.


1)1-(cyclobutylmethyl)-2,5-dimethylpiperidine + CH3I ------->1-(cyclobutylmethyl)-2,5-dimethylpiperidine methiodide
2)1-(cyclobutylmethyl)-2,5-dimethylpiperidine methiodide + C6H5SNa ------------>1,2,5-trimethylpiperidine + [(cyclobutylmethyl)sulfanyl]benzene + NaI



Now I'm pretty sure that step 1 proceeds with nothing more than a reagent in a solvent on or around RT. It's the second one whose details elude me. Now I'm pretty certain that the dequaternizing agent was (is?) sodium thiophenolate and it was simply a matter of the moiety removed was (is?) the more electron donating.

I know, I sound like (well, I am) an idiot. I gave my copy of Vogal's to one friend, my Merck Index to another friend... but only now do I realize that I sleepwalked through the inorganic chemistry lectures.

Cheers all,
CC

 

[sekio]

Something akin to this paper? (pdf)
Dealkylation of quaternary ammonium salts by thiolate anions: A model of the cobalamin-independent methionine synthase reaction.
https://doi.org/10.1016/S0040-4020(01)85267-4

Vogel's is availiable online, look around.

Also, this is still very much organic chemistry - in my mind you need to have predominantly non-hydrocarbons in your chemistry (e.g. salts and pure elements) to be "inorganic".

 

[clubcard]

Many thanks sekio. Your definition is quite right. The Eunoia disc only has a couple of mid-80s bits so that will be of value to students.

My best wishes to you and to everyone you care for.