Chemistry:1,1'-Ferrocenediisocyanate

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1,1'-Ferrocenediisocyanate
Fe(C5H4NCO)2.svg
Names
IUPAC name
1,1'-diisocyanatoferrocene
Identifiers
3D model (JSmol)
Properties
C12H8FeN2O2
Molar mass 268.053 g·mol−1
Appearance yellow-brown solid
Density 1.633 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,1'-Ferrocenediisocyanate (1,1'-diisocyanatoferrocene) is the organoiron compound with the formula Fe(C
5
H
4
NCO)
2
. It is the simplest diisocyanate derivative of ferrocene. It can be synthesized by the Curtius rearrangement of the diacyl azide, using several protocols starting from 1,1'-ferrocenedicarboxylic acid.[1] The compound is useful as an intermediate in the synthesis of 1,1'-diaminoferrocene by hydrolysis of the isocyanates.[1] Various poly(siloxaneurethane) crosslinked polymers can be formed by reaction with siloxane-diols.[2] These compounds are of interest as electrochemically active polymers that might have good mechanical properties at low temperature.

References

  1. 1.0 1.1 Petrov, Alex R.; Jess, Kristof; Freytag, Matthias; Jones, Peter G.; Tamm, Matthias (2013). "Large-Scale Preparation of 1,1′-Ferrocenedicarboxylic Acid, a Key Compound for the Synthesis of 1,1′-Disubstituted Ferrocene Derivatives". Organometallics 32 (20): 5946–5954. doi:10.1021/om4004972. 
  2. Dascalu, Mihaela; Musteata, Valentina E.; Vacareanu, Loredana; Racles, Carmen; Cazacu, Maria (2015). "Synthesis and characterization of metal-containing poly(siloxane-urethane) crosslinked structures derived from siloxane diols and ferrocene diisocyanate". RSC Advances 5 (120): 99193–99200. doi:10.1039/C5RA15290A. Bibcode2015RSCAd...599193D.