SUPPORTING INFORMATION
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1 SUPPORTING INFORMATION 1,1 -Biferrocenylenes The More Redox Stable Ferrocenes! New Derivatives, Corrected NMR Assignments, Redox Behavior and Spectroelectrochemistry Rochus Breuer, Michael Schmittel* Center of Micro and Nanochemistry and Engineering, Department of Chemistry and Biology, Organische Chemie I, Universität Siegen, Adolf-Reichwein-Str. 2, D Siegen, Germany Fax: (+49) Content: 1 H- 1 H-COSY and 1 H- 1 H-ROESY NMR of BFD derivatives pages S2-S16 Synthesis of BFD + PF 6 Synthesis of Fc + PF 6 References page S17 page S18 page S18 S1
2 1 H- 1 H-COSY and 1 H- 1 H-ROESY NMR assignments of the BFD derivatives 2a/b-6a/b, 7a/b, 8a/b Chemical shifts (δ) are reported in ppm and are referenced with regard to the residual protiated solvent, tetrachloroethane-d 2 : δ 5.91 ( 1 H) and δ 74.2 ( 13 C); chloroform-d 1 : δ 7.26 ( 1 H) and δ 77.0 ( 13 C); benzened 6 : δ 7.15 ( 1 H) and δ ( 13 C). The atom numbering system applied to the BFD system was proposed by Goldberg and Matteson. 1 S2
3 Figure S1. 1 H- 1 H-COSY-NMR of 2a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S2. 1 H- 1 H-ROESY-NMR of 2a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S3
4 Figure S3. 1 H- 1 H-COSY-NMR of 2b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S4. 1 H- 1 H-ROESY-NMR of 2b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S4
5 Figure S5. 1 H- 1 H-COSY-NMR of 3a (400 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S6. 1 H- 1 H-ROESY-NMR of 3a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S5
6 Figure S7. 1 H- 1 H-COSY-NMR of 3b (400 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S8. 1 H- 1 H-ROESY-NMR of 3b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S6
7 Figure S9. 1 H- 1 H-COSY-NMR of 4a (400 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S10. 1 H- 1 H-ROESY-NMR of 4a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S7
8 Figure S11. 1 H- 1 H-COSY-NMR of 4b (400 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S12. 1 H- 1 H-ROESY-NMR of 4b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S8
9 Figure S13. 1 H- 1 H-COSY-NMR of 5a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S14. 1 H- 1 H-ROESY-NMR of 5a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S9
10 Figure S15. 1 H- 1 H-COSY-NMR of 5b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S16. 1 H- 1 H-ROESY-NMR of 5b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S10
11 Figure S17. 1 H- 1 H-COSY-NMR of 6a (400 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S18. 1 H- 1 H-ROESY-NMR of 6a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S11
12 Figure S19. 1 H- 1 H-COSY-NMR of 6b (400 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S20. 1 H- 1 H-ROESY-NMR of 6b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S12
13 Figure S21. 1 H- 1 H-COSY-NMR of 7a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S22. 1 H- 1 H-ROESY-NMR of 7a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S13
14 Figure S23. 1 H- 1 H-COSY-NMR of 7b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S24. 1 H- 1 H-ROESY-NMR of 7b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S14
15 Figure S25. 1 H- 1 H-COSY-NMR of 8a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S26. 1 H- 1 H-ROESY-NMR of 8a (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S15
16 Figure S27. 1 H- 1 H-COSY-NMR of 8b (400 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) Figure S28. 1 H- 1 H-ROESY-NMR of 8b (600 MHz, C 2 D 2 Cl 4, shown is the region relevant for the BFD proton signals) S16
17 Synthesis of BFD + PF 6 according to a modified literature procedure. 2, 3 Cautionary warning on the handling of concentrated sulfuric acid! Observe safety precautions for handling concentrated sulfuric acid. Always wear eye protection and protective gloves. Concentrated sulfuric acid is corrosive to skin, metals and clothing and it will cause severe burns on contact with skin. Always add acid slowly to water. To 0.6 ml of conc. sulfuric acid was added 220 mg (0.600 mmol) of 1,1 -biferrocenylene. After stirring for 45 minutes, the dark-red solution was added slowly to a mixture of 300 mg t-butanol in 10 ml of water and stirred for 15 minutes. Insoluble parts were filtered off and at 0 C a solution of 440 mg (2.39 mmol) KPF 6 in 12 ml of water was added to the filtrate. After stirring for 1 h at 0 C the red precipitate was filtered off and washed twice with 10 ml portions of ice water, ethanol and finally with diethylether until the filtrate remained colourless. The red solid was placed in distilled water, heated to reflux and small portions of distilled water were added until a clear green solution was formed that was filtered hot. After some time a precipitate of dark-green, needlelike crystals was collected and dried in vacuum for 12 h. Yield: 140 mg (45%). Anal. Calcd for C 20 H 16 F 6 Fe 2 P: C 46.83, H Found C 46.96, H S17
18 Synthesis of Fc + PF 6 according to a literature procedure. 2 Cautionary warning on the handling of concentrated sulfuric acid! Observe safety precautions for handling concentrated sulfuric acid. Always wear eye protection and protective gloves. Concentrated sulfuric acid is corrosive to skin, metals and clothing and it will cause severe burns on contact with skin. Always add acid slowly to water. To 2.5 ml of conc. sulfuric acid was added 1.40 g (7.50 mmol) of ferrocene. After stirring for 45 minutes the dark-blue solution was added slowly to a mixture of 1.25 g t-butanol in 43 ml of water and stirred for 15 minutes. Insoluble parts were filtered off and at 0 C a solution of 2.80 g (15.0 mmol) KPF 6 in 60 ml of water was added to the filtrate. After stirring for 1 h at 0 C the blue precipitate was filtered off and washed twice with 10 ml portions of ice water, ethanol and finally with diethylether until the filtrate remained colourless. The blue solid was dried in vacuum for 12 h. Yield: 2.00 g (81%). Anal. Calcd for C 10 H 10 F 6 FeP: C 36.29, H Found C 36.50, H References 1 Goldberg, S. I.; Matteson, R. L. J. Org. Chem. 1964, 29, Jahn, U.; Hartmann, P.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2001, LeVanda, C.; Bechgaard, K.; Cowan, D. O.; Mueller-Westerhoff, U. T.; Eilbracht, P.; Candela, G. A.; Collins, R. L. J. Am. Chem. Soc. 1976, 98, S18
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