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We have developed a synthetic sequence to obtain [1,1]ferrocenophane in good yield and in a relatively simple way. The synthetic steps are outlined below.
English (United States)
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Synthesis of Mixed Metal Metallocenophanes
We have developed a synthetic sequence to obtain [1,1]ferrocenophane in
good yield and in a relatively simple way. The synthetic steps are outlined below.
The first step is a new addition reaction of 1,1'-dilithioferrocene to a fulvene.
No such reactions have been reported previously. The product of this reaction is
1,1'-bis-(6-fulvenyl-) ferrocene, obtained in better than 80% yield. This compound
was previously prepared by us from fulvenylcyclopentadienide and ferrous
chloride in a less advantageous way. It is a deep red crystalline material with
m.p. 112 degrees The next step is its reaction with lithium triethylborohydride or
other trialkyl borohydrides to produce the 1.1'-bis-cyclopentadienylmethyl-
ferrocene. This reaction has a great advantage over previous attempts in that the
only byproduct is the relatively inert triethyl boron, which does not interfere with
the further reaction with transition metal salts. The final step is the addition of
ferrous chloride to the dianion to produce the [1,1]-ferrocenophane in 40 to 50%
yield. Other metal salts may also be used, therefore opening the way to the
preparation of mixed metal metallocenophanes.