Mikael_Bakunin (Stranger)
01-03-04 15:24
No 480313
      Lewis acids in Friedel-Crafts alkylations     

Searching turned up:
Post 439768 (Lego: "P2Ps from benzenes by Friedel-Crafts reaction", Methods Discourse)

In this reference the authors alkylate benzene with an substituted monochloroacetone derivate. They use SnCl4 for this purpose and tell the activity of catalysts, Lewis-acids usable in this synthesis is:
AlCl3 = SnCl4 > TiCl4 > ZnCl2

This baffled me as up to now I thought the activity is more like:
AlCl3 > FeCl3 > SnCl4 = ZnCl2

At least this is what most literature I read on this reaction said also there was no real consens - only SnCl4 was widely regarded as being not very active.

If SnCl4 is usable for a chloroacetone - benzene coupling I hope this might help to avoid excessive polymerization/polyalkylation.

Has somebody experiences or otherwise knowledge on Friedel-Crafts alkylations with other Lewis acids than AlCl3, preferable with benzene as aromatic compound?


btw. my question is on Lewis acids, not on the dangers of chloroacetone - this compound seems to trigger rather hysteric outbreaks it seems.
 
 
 
 
    Major_Armstrong
(Stranger)
01-04-04 19:22
No 480427
      See Post 255616 Post 255661     

See
Post 255616 (PolytheneSam: "Re: Substituted P2P's:  Would this work?", Novel Discourse)
Post 255661 (PolytheneSam: "Re: Substituted P2P's:  Would this work?", Novel Discourse)
 
 
 
 
    Mikael_Bakunin
(Stranger)
01-06-04 05:18
No 480734
      Thanks Major     

Thats quite a lot to read - I will go over it and ask again so need is.
Hydrated ferric chloride - this to work on a unsubstituted benzene ring would be the hit of course.

Reading time again.

God is always with the bigger guns - Napoleon Bonaparte