Diastereomerically enriched analogues of the water-soluble phosphine PTA. Synthesis of phenyl(1,3,5-triaza-7-phosphatricyclo[3.3.1.13,7]dec-6- yl)methanol (PZA) and the sulfide PZA(S) and X-ray crystal structures of the oxide PZA(O) and [Cp*IrCl2(PZA)]

Inorganic Chemistry

Volumn 47, Issue 1, 2008, Pages 8-10

  Erlandsson, Mikael ^a   Gonsalvi, Luca ^a   Ienco, Andrea ^a   Peruzzini, Maurizio ^a  

^a ICCOM CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 TRIAZA 7 PHOSPHAADAMANTANE; 1,3,5-TRIAZA-7-PHOSPHAADAMANTANE; ADAMANTANE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; INORGANIC SALT; IRIDIUM; LITHIUM; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; OXIDE; PHENYL(1,3,5 TRIAZA 7 PHOSPHATRICYCLO(3.3.1.1(3,7))DEC 6 YL)METHANOL; PHENYL(1,3,5-TRIAZA-7-PHOSPHATRICYCLO(3.3.1.1(3,7))DEC-6-YL)METHANOL; PHOSPHINE DERIVATIVE; SULFIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; SOLUBILITY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ADAMANTANE; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS, 3-RING; IRIDIUM; LITHIUM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; OXIDES; PHOSPHINES; SALTS; SOLUBILITY; STEREOISOMERISM; SULFIDES; WATER;

EID: 38749139315     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic701795y     Document Type: Article

References (45)

1. Daigle, D. J.; Pepperman, A. B., Jr.; Vail, S. L. J. Heterocycl. Chem. 1974, 11, 407-408.
2. For a review on coordination chemistry and the use of PTA covering the literature up to the beginning of 2004, see: Phillips, A. D.; Gonsalvi, L.; Romerosa, A.; Vizza, F.; Peruzzini, M. Coord. Chem. Rev. 2004, 248, 955-993 and references cited therein.
3. (a) Bolaño, S.; Gonsalvi, L.; Zanobini, F.; Vizza, F.; Bertolasi, V.; Romerosa A.; Peruzzini, M. J. Mol. Catal. A: Chem. 2004, 224, 61-70.
4. (b) Horváth, H.; Laurenzy, G.; Katho, A. J. Organomet. Chem. 2004, 689, 1036-1045.
5. (c) Mebi, C. A.; Frost, B. J. Organometallics 2005, 24, 2339-2346.
6. (d) Krogstad, D. A.; Cho, J.; DeBoer, A. J.; Klitzke, J. A.; Sanow, W. R.; Williams, H. A.; Halfen, J. A. Inorg. Chim. Acta 2006, 359, 136-148.
7. (e) Krogstad, D. A.; Owens, S. B.; Halfen, J. A.; Young, V. G., Jr. Inorg. Chem. Commun. 2005, 8, 65-69.
8. (f) Krogstad, D. A.; DeBoer, A. J.; Ortmeier, W. J.; Rudolf, J. W.; Halfen, J. A. Inorg. Chem. Commun. 2005, 8, 1141-1144.
9. (g) Ruiz, J.; Cutillas, N.; López, F.; López, G.; Bautista, D. Organometallics 2006, 25, 5768-5773.
10. (h) Korthals, B.; Göttker-Schnetmann, I.; Meckirg, S. Organometallics 2007, 26, 1311-1316.
11. (i) Mebi, C. A.; Nair, R. P.; Frost, B. J. Organometallics 2007, 26, 429-438.
12. (a) Ang, W. H.; Daldini, E.; Scolaro, C.; Scopelliti, R.; Juillerat-Jennerat, L.; Dyson, P. J. Inorg. Chem. 2006, 45, 9006-9013.
13. (b) Scolaro, C.; Bergamo, A.; Brescacin, L.; Delfino, R.; Cocchietto, M.; Laurenczy, G.; Geldbach, T. J.; Sava, G.; Dyson, P. J. J. Med. Chem. 2005, 48, 4161-4171.
14. (c) Dorcier, A.; Dyson, P. J.; Gossens, C.; Rothlisberger, U.; Scopelliti, R.; Tavernelli, I. Organometallics 2005, 24, 2114-2123.
15. (d) Dorcier, A.; Ang, W. H.; Bolaño, S.; Gonsalvi, L.; Juilleratt-Jennerat, L.; Laurenczy, G.; Peruzzini, M.; Phillips, A. D.; Zanobini, F.; Dyson, P. J. Organometallics 2006, 25, 4090-4096.
16. (e) Ang, W. H.; Dyson, P. J. Eur. J. Inorg. Chem. 2006, 4003-4018.
17. (f) Romerosa, A.; Campos-Malpartida, T.; Lidrissi, C.; Saoud, M.; Serrano-Ruiz, M.; Peruzzini, M.; Garrido-Cardenas, J. A.; García-Maroto, F. Inorg. Chem. 2006, 45, 1289-1298.
18. (g) Romerosa, A.; Saoud, M.; Campos-Malpartida, T.; Lidrissi, C.; Serrano-Ruiz, M.; Peruzzini, M.; Garrido, J. A.; García-Maroto, F. Eur. J. Inorg. Chem. 2007, 2803-2812.
19. Gutkin, V.; Gun, J.; Prikhodehenko, P. V.; Lev, O.; Romerosa, A.; Campos Malpartida, T.; Lidrissi, C.; Gonsalvi, L.; Peruzzini, M. J. Electrochem. Soc. 2007, 154, F7-F15.
20. Rossin, A.; Gonsalvi, L.; Phillips, A. D.; Maresca, O.; Lledos, A.; Peruzzini, M. Organometallics 2007, 26, 3289-3296.
21. (a) Daigle, D. J.; Pepperman, A. B., Jr. J. Heterocycl. Chem. 1975, 12, 579-580.
22. (b) Fluck, E.; Weissgraeber, H. J. Chem.-Ztg. 1977, 101, 304.
23. (c) Fluck, E.; Förster, J. E.; Weidlein, J.; Hädicke, E. Z. Naturforsch. 1977, 32, 499-506.
24. (d) Forward, J. M.; Staples, R. J.; Fackler, J. P., Jr. Z. Kristallogr. 1996, 211, 129-130.
25. (e) Smolenski, P.; Pruchnik, F. P.; Ciunik, Z.; Lis, T. Inorg. Chem. 2003, 42, 3318-3322.
26. (a) Daigle, D. J.; Boudreaux, G. J.; Vail, S. L. J. Chem. Eng. Data 1976, 21, 240-241.
27. (b) Siele, V. I. J. Heterocycl. Chem. 1977, 14, 337-339.
28. (c) Navech, J.; Kraimer, R.; Majoral, J. P. Tetrahedron Lett. 1980, 21, 1449-1452.
29. (d) Darensbourg, D. J.; Yarbrough, J. C.; Lewis, S. J. Organometallics 2003, 22, 2050-2056.
30. (a) Assmann, B.; Angermaier, K.; Schmidbaur, H. J. Chem. Soc., Chem. Commun. 1994, 941-942.
31. (b) Assmann, B.; Angermaier, K.; Paul, M.; Schmidbaur, H. Chem. Ber. 1995, 128, 891-900.
32. (c) Phillips, A. D.; Bolaño, S.; Bosquain, S. S.; Daran, J.-C.; Malacea, R.; Peruzzini, M.; Poli, R.; Gonsalvi, L. Organometallics 2006, 25, 2189-2200.
33. Mena-Cruz, A.; Lorenzo-Luis, P.; Romerosa, A.; Saoud, M.; Serrano-Ruiz, M. Inorg. Chem. 2007, 46, 6120-6128.
34. Wong, G. W.; Harkreader, J. L.; Mebi, C. A.; Frost, B. J. Inorg. Chem. 2006, 45, 6748-6755.
35. For the synthesis of PTA(S), see: Fischer, K. J.; Alyea, E. C.; Shahnazarian, N. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 48, 37-40.
36. Daigle, D. J. Inorg. Synth. 1998, 32, 40-48.
37. White, C.; Yates, A.; Maitlis, P. Inorg. Synth. 1992, 29, 228-234.
38. (a) Darensbourg, D. J.; Stafford, N. W.; Joó, F.; Reibenspies, J. H. J. Organomet. Chem. 1995, 488, 99-108.
39. (b) Jogun, K. H.; Stezowski, J. J.; Fluck, E.; Weidlein, J. Phosphorus Sulfur Relat. Elem. 1978, 4, 199-204.
40. (c) Marsh, R. E.; Kapon, M.; Hu, S.; Herbstein, F. H. Acta Crystallogr., Sect. B: Struct. Sci. 2002, 58, 62-77.
41. Erlandsson, M.; Landaeta, V. R.; Gonsalvi, L.; Peruzzini, M.; Phillips, A. D.; Dyson, P. J.; Laurenczy, G. Eur. J. Inorg. Chem. 2007, DOI: 10.1002/ejic.200700792.
42. 3, collected/unique = 2408/2277 [R(int) = 0.0587], R1 = 0.0787, wR2 = 0.1391 [I > 2σ(I)]; R1 = 0.1930, wR2 = 0.1708 (all data). The data collection was performed at room temperature on an Enraf Nonius CAD4 diffractometer equipped with a graphite monochromator and Mo Kα radiation. Selected bond distances (Å) and angles (deg): P(1)-O(2), 1.490(4); P(1)-C(1), 1.833(6); P(1)-C(2) 1.808(6); P(1)-C(3), 1.818(5); N(1)-C(1), 1.502(6); N(1)-C(4), 1.469(8); N(1)-C(6), 1.468(7); N(2)-C(2), 1.493(7); N(2)-C(4), 1.457(8); N(2)-C(5), 1.461(8); N(3)-C(3), 1.485(7); N(3)-C(5), 1.461(8); N(3)-C(6), 1.455(7); C(1)-C(7), 1.527(7); O(2)-P(1)-C(1), 117.7(2); O(2)-P(1)-C(2), 117.7(3); O(2)-P(1)-C(3), 115.0-(2); C(1)-P(1)-C(2), 103.7(3); C(1)-P(1)-C(3), 100.0(3); C(2)-P(1)-C(3), 100.0(3); C(1)-N(1)-C(4), 112.3(4); C(1)-N(1)-C(6), 111.4(4); C(2)-N(2)-C(4), 110.0(4); C(2)-N(2)-C(5), 110.7(5); C(3)-N(3)-C(5), 110.0(5); C(3)-N(3)-C(6), 109.8(4); C(4)-N(1)-C(6), 108.4(5); C(4)-N(2)-C(5), 109.3(5); C(5)-N(3)-C(6), 108.3(5).
43. The symmetry transformation used to generate the equivalent atom is as follows: #1, -x + 1, y + 1/2, -z + 1/2.
44. Frost, B. J.; Mebi, C. A.; Gingrich, P. W. Eur. J. Inorg. Chem. 2006, 1182.
45. 3, collected/unique = 16383/7502 [R(int) = 0.0294], absorption correction = Ψ scan, R1 = 0.0292, wR2 = 0.0557 [I > 2σ(I)]; R1 = 0.0600, wR2 = 0.0671 [all data]. The data collection was performed at room temperature on an Oxford Diffraction Excalibur 3 diffractometer equipped with Mo Kα radiation. Selected bond distances (Å) and angles (deg): Ir(1)-P(1), 2.2971(9); Ir(1)-Cl(1), 2.4127(10); Ir(1)-Cl(2), 2.4273(10); Ir(1)-Cp*(centroid), 1.8187(16); P(1)-C(1), 1.864(4); P(1)-C(2), 1.853(4); P(1)-C(3), 1.837(4); O(1a)-Cl(2), 3.319(6); O(1b)-Cl(2), 3.112(6); P(1)-Ir(1)-Cl(1), 85.55(4); P(1)-Ir(1)-Cl(2), 88.70(4); Cl(1)-Ir(1)-Cl(2), 89.38(4); P(1)-Ir(1)- Cp*(centroid), 133.20(4); Cl(1)-Ir(1)-Cp*(centroid), 123.49(4); Cl(2)-Ir(1)-Cp*(centroid), 123.38(4).