Selenothiophosphinic acid salts: Efficient synthesis, structure and reactivity

Chemistry Letters

Volumn , Issue 9, 2002, Pages 914-915

  Murai, Toshiaki ^a   Kimura, Tsutomu ^a   Miwa, Akihiro ^a   Kurachi, Daisuke ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALI METAL; AMMONIA; ESTER DERIVATIVE; FLUORIDE; PHOSPHINIC ACID DERIVATIVE; SELENIUM DERIVATIVE;

ACYLATION; ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0037026849     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.914     Document Type: Article

References (21)

1. For a review: J. C. Tebby, D. G. Genov, and J. W. Wheeler, in "Comprehensive Organic Functional Group Transformation," ed. by A. R. Katritzky, O. Meth-Cohn, and C. W. Rees, Pergamon, Oxford (1995) Vol. 2, p 462.
2. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
3. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
4. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
5. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
6. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
7. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
8. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
9. For recent examples: W. E. Van-Zyl, J. M. Lopez-De-Luzuriaga, J. P. Fackler Jr., and R. J. Staples, Can. J. Chem., 79, 896 (2001); S. V. Larionov, V. G. Shchukin, L. A. Glinskaya, R. F. Klevtsova, and A. P. Mazhara, Russ. J. Coord. Chem., 27, 463 (2001); J. E. Drake, M. B. Hursthouse, M. Kulcsar, M. E. Light, and A. Silvestru, Phosphorus, Sulfur Silicon Relat. Elem., 168 & 169, 617 (2001); V. Garcia-Montalvo, A. Marcelo-Polo, R. Montoya, R. A. Tascano, S. Hernandez-Ortega, and R. Cea-Olivares, J. Organomet. Chem., 623, 74 (2001); V. Garcia-Montalvo, R. A. Tascano, A. Badillo-Delgado, and R. Cea-Olivares, Polyhedron, 20, 203 (2001); J.-H. Park, P. O'Brien, A. J. P. White, and D. J. Williams, Inorg. Chem., 40, 3629 (2001); S. Garcia-Fontan, E. Lamas-Castro, P. Rodriguez-Seoane, and E. M. Vazquez-Lopez, Acta Crystallogr., Sect. C, C57, 532 (2001); A. Silvestru, A. Rotar, J. E. Drake, M. B. Hursthouse, M. E. Light, S. I. Farcas, R. Rosler, and C. Silvestru, Can. J. Chem., 79, 983 (2001).
10. W. Kuchen and B. Knop, Angew. Chem., 76, 496 (1964).
11. H. Hertel and W. Kuchen, Chem. Ber., 104, 1735 (1971); H. Hertel and W. Kuchen, Chem. Ber., 104, 1740 (1971); P. Christophliemk, V. V. K. Rao, I. Tossidis, and A. Müller, Chem. Ber., 105, 1736 (1972); A. Mueller, V. V. K. Rao, and P. Christophliemk, J. Inorg. Nucl. Chem., 34, 345 (1972); S. Esperås and S. Husebye, Acta Chem. Scand., 27, 3355 (1973).
12. H. Hertel and W. Kuchen, Chem. Ber., 104, 1735 (1971); H. Hertel and W. Kuchen, Chem. Ber., 104, 1740 (1971); P. Christophliemk, V. V. K. Rao, I. Tossidis, and A. Müller, Chem. Ber., 105, 1736 (1972); A. Mueller, V. V. K. Rao, and P. Christophliemk, J. Inorg. Nucl. Chem., 34, 345 (1972); S. Esperås and S. Husebye, Acta Chem. Scand., 27, 3355 (1973).
13. H. Hertel and W. Kuchen, Chem. Ber., 104, 1735 (1971); H. Hertel and W. Kuchen, Chem. Ber., 104, 1740 (1971); P. Christophliemk, V. V. K. Rao, I. Tossidis, and A. Müller, Chem. Ber., 105, 1736 (1972); A. Mueller, V. V. K. Rao, and P. Christophliemk, J. Inorg. Nucl. Chem., 34, 345 (1972); S. Esperås and S. Husebye, Acta Chem. Scand., 27, 3355 (1973).
14. H. Hertel and W. Kuchen, Chem. Ber., 104, 1735 (1971); H. Hertel and W. Kuchen, Chem. Ber., 104, 1740 (1971); P. Christophliemk, V. V. K. Rao, I. Tossidis, and A. Müller, Chem. Ber., 105, 1736 (1972); A. Mueller, V. V. K. Rao, and P. Christophliemk, J. Inorg. Nucl. Chem., 34, 345 (1972); S. Esperås and S. Husebye, Acta Chem. Scand., 27, 3355 (1973).
15. H. Hertel and W. Kuchen, Chem. Ber., 104, 1735 (1971); H. Hertel and W. Kuchen, Chem. Ber., 104, 1740 (1971); P. Christophliemk, V. V. K. Rao, I. Tossidis, and A. Müller, Chem. Ber., 105, 1736 (1972); A. Mueller, V. V. K. Rao, and P. Christophliemk, J. Inorg. Nucl. Chem., 34, 345 (1972); S. Esperås and S. Husebye, Acta Chem. Scand., 27, 3355 (1973).
16. For multi-step synthesis of selenothiophosphinic acid salts: S. Kato, M. Goto, R. Hattori, K. Nishiwaki, M. Mizuta, and M. Ishida, Chem. Ber., 118, 1668 (1985).
17. For synthesis of optically active selenothiophosphinic acid salt: Z. Skrzypczynski and J. Michalski, J. Org. Chem., 53, 4549 (1988).
18. 6PSSe: C, 45.59; H, 6.61. Found: C, 45.31, H, 6.56.
19. P-Se = 762.2 Hz.
20. w = 0.141, 6293 reflections (I > 3σ(I)). The selenium or sulfur atom appeared at the position [E(1)] or at the position [E(2)] shown in Figure 1. The occupancy of the selenium atom is 0.37 in [E(1)] and 0.63 in [E(2)], respectively, and the reverse results are obtained for the sulfur atom.
21. The starting salts 2 were also recovered, but the reaction at higher temperatures did not necessarily gave the products in better yields mainly because of the decomposition of the products formed.