Vinylferrocene

Vinylferrocene
Names
IUPAC name
Vinylferrocene
Systematic IUPAC name
Ethenylferrocene
Other names
Ferrocenylethene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/2C7H7.2C5H5.2Fe/c2*1-2-7-5-3-4-6-7;2*1-2-4-5-3-1;;/h2*2-6H,1H2;2*1-5H;;/q4*-1;2*+2
    Key: VXSUCWUFYMRJEK-UHFFFAOYSA-N
  • C=C[C-]1C=CC=C1.C=C[C-]1C=CC=C1.[CH-]1C=CC=C1.[CH-]1C=CC=C1.[Fe+2].[Fe+2]
Properties
C12H12Fe
Molar mass 212.073 g·mol−1
Appearance orange solid
Melting point 50–52 °C (122–126 °F; 323–325 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vinylferrocene is the organometallic compound with the formula (C5H5)Fe(C5H4CH=CH2). It is a derivative of ferrocene, with a vinyl group attached to one cyclopentadienyl ligand. As the ferrocene analogue of styrene, it is the precursor to some polyferrocenes.[1] It is an orange, air-stable oily solid that is soluble in nonpolar organic solvents.

Vinylferrocene can be prepared by the dehydration of α-hydroxylethylferrocene, which is obtained from acetylferrocene.[2] It can also be made by a Wittig reaction of ferrocenecarboxaldehyde.[3]

References

  1. ^ Cass, Anthony E. G.; Davis, Graham; Francis, Graeme D.; Hill, H. Allen O.; Aston, William J.; Higgins, I. John; Plotkin, Elliot V.; Scott, Lesley D. L.; Turner, Anthony P. F. (1984). "Ferrocene-mediated enzyme electrode for amperometric determination of glucose". Analytical Chemistry. 56 (4): 667–671. doi:10.1021/ac00268a018. PMID 6721151.
  2. ^ Rausch, Marvin D.; Siegel, Armand (1968). "Organometallic π-complexes. XIV. Vinylmetallocenes". Journal of Organometallic Chemistry. 11: 317–324. doi:10.1016/0022-328X(68)80054-3.
  3. ^ Liu WY, Xu QH, Ma YX, Liang YM, Dong NL, Guan DP (2001). "Solvent-free synthesis of ferrocenylethene derivatives". J. Organomet. Chem. 625: 128–132. doi:10.1016/S0022-328X(00)00927-X.