Novel Fluorinated Phosphorus–Sulfur Heteroatom Compounds: Synthesis and Characterization of Ferrocenyl- and Aryl-Phosphonofluorodithioic Salts, Adducts, and Esters
Abstract
:1. Introduction
2. Results and Discussion
Compound | 3 | 13 | 14 | 18 |
---|---|---|---|---|
Formula | C34H29FFeP2S2 | C34H26FOP3S3 | C30H22FN3OP3S3 | C10H6O2P2S4 |
M | 638.52 | 658.68 | 617.65 | 348.34 |
Crystal system | Monoclinic | Monoclinic | Triclinic | Monoclinic |
Space group | P21/n | P21/c | P-1 | P21/n |
a/Å | 11.704(2) | 9.563(3) | 9.992(4) | 11.171(3) |
b/Å | 17.994(2) | 16.876(5) | 16.808(8) | 8.618(2) |
c/Å | 14.981(3) | 19.258(6) | 18.117(8) | 14.122(4) |
α | 90 | 90 | 104.020(11) | 90 |
β | 106.902(9) | 93.820(7) | 90.270(10) | 99.002(6) |
γ | 90 | 90 | 104.404(11) | 90 |
U/A3 | 3018.6(9) | 3101.1(15) | 2852(3) | 1342.8(6) |
Z | 4 | 4 | 4 | 4 |
µ/mm−1 | 7.726 | 4.277 | 4.090 | 9.32 |
Reflections collected | 25,726 | 23,431 | 21,800 | 9765 |
Independent reflections | 5310 | 5430 | 9960 | 2346 |
Rint | 0.1707 | 0.1124 | 0.1052 | 0.0696 |
R1 | 0.0824 | 0.1037 | 0.0988 | 0.0526 |
wR2 [I > 2σ(I)] | 0.0912 | 0.2408 | 0.2433 | 0.1339 |
3. Experimental Section
3.1. General
3.2. Synthesis
3.2.1. Synthesis of Potassium Ferrocenylphosphonofluoridodithioate (1)
3.2.2. Synthesis of Tetrabutylammonium Ferrocenylphosphonofluoridodithioate (2)
3.2.3. Synthesis of Tetraphenylphosphonium Ferrocenylphosphonofluoridodithioate (3)
3.2.4. Synthesis of 1,4-Phenylenebis(methylene) Bis(ferrocenylphosphonofluoridodithioate) (4)
3.2.5. Synthesis of 4-Nitrobenzyl Ferrocenylphosphonofluoridodithioate (5)
3.2.6. Synthesis of 4-Bromobenzyl Ferrocenylphosphonofluoridodithioate (6)
3.2.7. Synthesis of Methylyl Ferrocenylphosphonofluoridodithioate (7)
3.2.8. Synthesis of 4-Cyanobenzyl Ferrocenylphosphonofluoridodithioate (8)
3.2.9. Synthesis of Benzyl Ferrocenylphosphonofluoridodithioate (9)
3.2.10. Synthesis of Potassium3-fluoronaphtho[1,8-cd][1,2,6]oxadiphosphinine-1(3H)-thiolate 1,3-disulfide (11)
3.2.11. Synthesis of Tetrabutylammonium 3-fluoronaphtho[1,8-cd][1,2,6]oxadiphosphinine-1(3H)-thiolate 1,3-disulfide (12)
3.2.12. Synthesis of Tetraphenylphosphonium3-fluoronaphtho[1,8-cd][1,2,6]oxadiphosphinine-1(3H)-thiolate 1,3-disulfide (13)
3.2.13. Synthesis of 1,3,4-Triphenyl-1H-1,2,4-triazol-4-ium3-fluoronaphtho[1,8-cd][1,2,6]oxadiphosphinine-1(3H)-thiolate 1,3-disulfide (14)
3.2.14. Synthesis of 1,3-Dimesityl-4,5-dihydro-1H-imidazol-3-ium3-fluoronaphtho[1,8-cd][1,2,6]oxadiphosphinine-1(3H)-thiolate 1,3-disulfide (15)
3.2.15. Synthesis of 1,5-Epoxynaphtho[1,8-cd][1,7,2,6]dithiadiphosphocine 1,5-disulfide (18)
3.2.16. Synthesis of Potassium (4-phenoxyphenyl)phosphonofluoridodithioate (19)
3.2.17. Synthesis of Tetrabutylammonium (4-phenoxyphenyl)phosphonofluoridodithioate (20)
3.2.18. Synthesis of Tetraphenylphosphonium (4-phenoxyphenyl)phosphonofluoridodithioate (21)
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Hua, G.; Du, J.; Surgenor, B.A.; Slawin, A.M.Z.; Woollins, J.D. Novel Fluorinated Phosphorus–Sulfur Heteroatom Compounds: Synthesis and Characterization of Ferrocenyl- and Aryl-Phosphonofluorodithioic Salts, Adducts, and Esters. Molecules 2015, 20, 12175-12197. https://doi.org/10.3390/molecules200712175
Hua G, Du J, Surgenor BA, Slawin AMZ, Woollins JD. Novel Fluorinated Phosphorus–Sulfur Heteroatom Compounds: Synthesis and Characterization of Ferrocenyl- and Aryl-Phosphonofluorodithioic Salts, Adducts, and Esters. Molecules. 2015; 20(7):12175-12197. https://doi.org/10.3390/molecules200712175
Chicago/Turabian StyleHua, Guoxiong, Junyi Du, Brian A. Surgenor, Alexandra M. Z. Slawin, and J. Derek Woollins. 2015. "Novel Fluorinated Phosphorus–Sulfur Heteroatom Compounds: Synthesis and Characterization of Ferrocenyl- and Aryl-Phosphonofluorodithioic Salts, Adducts, and Esters" Molecules 20, no. 7: 12175-12197. https://doi.org/10.3390/molecules200712175