Transannular interactions in mixed superphanes with one thiophene and one cpco-stabilized cyclobutadiene ring: syntheses, structures, and electrochemistry

Superphanes consisting of one thiophene ring and various substituted RCo-stabilized cyclobutadiene (CBD) rings (R = Cp, C5H4(CH3), C5(CH3)5, C5H4(Si(CH3)3), C5H4(COCH3), 8−12) and one superphane with one thiophene ring and one CpCo-stabilized cyclopentadienone ring (13) were synthesized. The startin...

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Bibliographic Details
Main Authors: Stäb, Silke (Author) , Gleiter, Rolf (Author) , Rominger, Frank (Author) , Bleiholder, Christian (Author)
Format: Article (Journal)
Language:English
Published: January 5, 2007
In: Organometallics
Year: 2007, Volume: 26, Issue: 3, Pages: 644-650
ISSN:1520-6041
DOI:10.1021/om0608206
Online Access:Verlag, Volltext: http://dx.doi.org/10.1021/om0608206
Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/abs/10.1021/om0608206
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Author Notes:Silke Gath, Rolf Gleiter, Frank Rominger, and Christian Bleiholder
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Summary:Superphanes consisting of one thiophene ring and various substituted RCo-stabilized cyclobutadiene (CBD) rings (R = Cp, C5H4(CH3), C5(CH3)5, C5H4(Si(CH3)3), C5H4(COCH3), 8−12) and one superphane with one thiophene ring and one CpCo-stabilized cyclopentadienone ring (13) were synthesized. The starting point was a tricyclic diyne with a central thiophene ring and two condensed 4-cyclodecynes, 19. Heating of 19 with RCo(COD) yielded 8−12, whereas the heating of 19 with CpCo(CO)2 gave 13. X-ray structural investigation of 8−13 afforded the geometrical parameters in the solid state. Cyclic voltammetry showed a strong interaction between the thiophene ring and the CpCo-stabilized cyclobutadiene part. This interaction was substantiated by comparison between the CV data of 8−12 and model systems containing only the CpCo(CBD) part.
Item Description:Gesehen am 28.09.2017
Physical Description:Online Resource
ISSN:1520-6041
DOI:10.1021/om0608206