Hockeydemon
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Registered: 25-2-2013
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hexaferrocenylbenzene via Negishi coupling
I know this is so far beyond me, but I thought the molecule was very interesting looking
Anyways is this something that no hobby chemist could form for the most part? I get that it is 'the impossible chemical' - I figured I'd share it
either way.
One could go 1-butanol + HCl --> Chlorobutane
Then Chlorobutane + Lithium --> n-Butyllithium
Then via halogen lithium exchange for vinyllithium
Then perform a Negishi coupling of hexaiodidobenzene, diferrocenylzinc and tris(dibenzylideneacetone)dipalladium(0) in tetrahydrofuran
tris(dibenzylideneacetone)dipalladium(0) can be prepared from Sodium tetrachloropalladate & Dibenzylideneacetone
Dibenzylideneacetone can be prepared via an adol condensation of benzaldehyde, acetone & NaOH.
Sodium tetrachloropalladate can be prepared by reacting palladium(II) chloride with an alkli metal to form the salt.
& diferrocenylzinc can be prepared from iodoferrocene13 by lithiation with Butyllithium followed by zincation with ZnBr2
Granted I haven't even heard of the chemicals being coupled in the Negishi reaction
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kristofvagyok
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If you have a proper and well equipped lab with all the reagents and a lot experience, than you could do this in a few month, maybe a year. But if you
are new in organic chemistry and have limited access to these reagents, and also you would like to make everything from nothing, than forget it in
time.
Just a few things to note: in lab we usually don't make n-BuLi and Pd2(dba)3 ect, these are easily available reagents. Harder to make, than buy it.
Another question: if you would like to do the reaction from: Chemical Communications (Cambridge, United Kingdom), 2006 , # 24 p. 2572 - 2574, than
it is important to note that they report a 4% yield for the title compound what is really not that much, so I wouldn't even start on this route, looks
bad.
I was once interested in polysubstitued benzenes, mainly where every hydrogen was replaced by a thiophene or a furan, maybe a pyrrole. The synthesis
of the hexathiophenyl-benzene is the most promising, it needs di-3-thienyl-acetylene, some RhCl3 and a little base (diisopropyl-ethylamine). The
synthesis has a reported 23% yield what is not that bad, according to: Tetrahedron, 2008 , vol. 64, # 24 p. 5800 - 5807.
I have a blog where I post my pictures from my work: http://labphoto.tumblr.com/
-Pictures from chemistry, check it out(:
"You can’t become a chemist and expect to live forever." |
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