(Bis{2,4,6-triisopropylphenyl}stannylene)ferrocenophane and related ring-opened products

Citation
Hk. Sharma et al., (Bis{2,4,6-triisopropylphenyl}stannylene)ferrocenophane and related ring-opened products, ORGANOMETAL, 18(3), 1999, pp. 399-403
Citations number
39
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
02767333 → ACNP
Volume
18
Issue
3
Year of publication
1999
Pages
399 - 403
Database
ISI
SICI code
0276-7333(19990201)18:3<399:(ARR>2.0.ZU;2-V
Abstract
The addition of bis(2,4,6-triisopropylphenyl)tin dichloride (1) to a hexane /THF slurry of 1,1'-dilithioferrocene-tmeda produces the corresponding stan nyleneferrocenophane (2) in good yield. Structural analysis of 2 reveals a dihedral angle between the two cyclopentadienyl rings of 14.7 degrees and a relatively short Fe-Sn atomic distance of 2.994(2) Angstrom. Cyclic voltam metry of 2 exhibits reversible redox behavior. Whereas treatment with MeOH and H2O failed to produce ring-opened compounds, silica gel catalyzed hydro lysis of 1 leads to ring-opened Fc(i-Pr3C6H2)(2)SnOH (3), which crystallize s as a H-bonded dimer. Thermal treatment of 2 at 180 degrees C leads to the ring-opened polymerization product 4, which after precipitation from tolue ne remains insoluble in organic solvents. Solid-state C-13 and Sn-119 NMR s pectra of 4 confirm the structure of the material. The X-ray structural ana lysis of 1 is reported and compared to that of 2.