Novel room light-induced disproportionation reaction of organo-ditin and -dilead compounds with organic dichalcogenides: An efficient salt-free route to organo-tin and -lead chalcogenides

Chemical Communications

Volumn , Issue 8, 2000, Pages 657-658

  Mirzaei, Farzad ^a   Han, Li Biao ^a   Tanaka, Masato ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHALCOGEN; LEAD; ORGANOTIN COMPOUND;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOREACTIVITY; REACTION ANALYSIS; SEMICONDUCTOR; SYNTHESIS;

EID: 0034696910     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b000309n     Document Type: Article

References (30)

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5. For reviews, see: D. A. Armitage, in The Silicon-Heteroatom Bond, ed. S. Patai and Z. Rappoport, John Wiley and Sons, Chichester, 1991, pp. 213-243; Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 2, pp. 34-37, 166-174, 293-296; Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1982, vol. 2, pp. 167-177, 443-447, 604-607. See also: Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita, Bull Chem. Soc. Jpn., 1985, 58, 3657; Y. Nishiyama, S. Aoyama and S. Hatanaka, Phosphorus, Sulfur Silicon Relat. Elem., 1992, 67, 267; Y. Nishiyama, H. Ohashi, K. Itoh and N. Sonoda, Chem. Lett., 1998, 159.
6. For reviews, see: D. A. Armitage, in The Silicon-Heteroatom Bond, ed. S. Patai and Z. Rappoport, John Wiley and Sons, Chichester, 1991, pp. 213-243; Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 2, pp. 34-37, 166-174, 293-296; Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1982, vol. 2, pp. 167-177, 443-447, 604-607. See also: Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita, Bull Chem. Soc. Jpn., 1985, 58, 3657; Y. Nishiyama, S. Aoyama and S. Hatanaka, Phosphorus, Sulfur Silicon Relat. Elem., 1992, 67, 267; Y. Nishiyama, H. Ohashi, K. Itoh and N. Sonoda, Chem. Lett., 1998, 159.
7. For reviews, see: D. A. Armitage, in The Silicon-Heteroatom Bond, ed. S. Patai and Z. Rappoport, John Wiley and Sons, Chichester, 1991, pp. 213-243; Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 2, pp. 34-37, 166-174, 293-296; Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1982, vol. 2, pp. 167-177, 443-447, 604-607. See also: Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita, Bull Chem. Soc. Jpn., 1985, 58, 3657; Y. Nishiyama, S. Aoyama and S. Hatanaka, Phosphorus, Sulfur Silicon Relat. Elem., 1992, 67, 267; Y. Nishiyama, H. Ohashi, K. Itoh and N. Sonoda, Chem. Lett., 1998, 159.
8. For reviews, see: D. A. Armitage, in The Silicon-Heteroatom Bond, ed. S. Patai and Z. Rappoport, John Wiley and Sons, Chichester, 1991, pp. 213-243; Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 2, pp. 34-37, 166-174, 293-296; Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1982, vol. 2, pp. 167-177, 443-447, 604-607. See also: Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita, Bull Chem. Soc. Jpn., 1985, 58, 3657; Y. Nishiyama, S. Aoyama and S. Hatanaka, Phosphorus, Sulfur Silicon Relat. Elem., 1992, 67, 267; Y. Nishiyama, H. Ohashi, K. Itoh and N. Sonoda, Chem. Lett., 1998, 159.
9. For reviews, see: D. A. Armitage, in The Silicon-Heteroatom Bond, ed. S. Patai and Z. Rappoport, John Wiley and Sons, Chichester, 1991, pp. 213-243; Comprehensive Organometallic Chemistry II, ed. E. W. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 2, pp. 34-37, 166-174, 293-296; Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, Oxford, 1982, vol. 2, pp. 167-177, 443-447, 604-607. See also: Kosugi, T. Ogata, M. Terada, H. Sano and T. Migita, Bull Chem. Soc. Jpn., 1985, 58, 3657; Y. Nishiyama, S. Aoyama and S. Hatanaka, Phosphorus, Sulfur Silicon Relat. Elem., 1992, 67, 267; Y. Nishiyama, H. Ohashi, K. Itoh and N. Sonoda, Chem. Lett., 1998, 159.
10. L.-B. Han and M. Tanaka, J. Am. Chem. Soc., 1998, 120, 8249.
11. 2 (Z = S, Se, Te) are also known: R. S. Dickson and K. D. Heazle, J. Organomet. Chem., 1995, 493, 189; W. Uhl, M. Layh, G. Becker, K.-W. Klinkhammer and T. Hildenbrand, Chem. Ber., 1992, 125, 1547; H. J. Breuning and S. Guelec, Z. Naturforsch., Teil B, 1986, 41, 1387; A. J. Ashe III and E. G. Ludwig, Jr., J. Organomet. Chem., 1986, 308, 289; W. W. du Mont, T. Severengiz and H. J. Breuning, Z. Naturforsch., Teil B, 1983, 38, 1306.
12. 2 (Z = S, Se, Te) are also known: R. S. Dickson and K. D. Heazle, J. Organomet. Chem., 1995, 493, 189; W. Uhl, M. Layh, G. Becker, K.-W. Klinkhammer and T. Hildenbrand, Chem. Ber., 1992, 125, 1547; H. J. Breuning and S. Guelec, Z. Naturforsch., Teil B, 1986, 41, 1387; A. J. Ashe III and E. G. Ludwig, Jr., J. Organomet. Chem., 1986, 308, 289; W. W. du Mont, T. Severengiz and H. J. Breuning, Z. Naturforsch., Teil B, 1983, 38, 1306.
13. 2 (Z = S, Se, Te) are also known: R. S. Dickson and K. D. Heazle, J. Organomet. Chem., 1995, 493, 189; W. Uhl, M. Layh, G. Becker, K.-W. Klinkhammer and T. Hildenbrand, Chem. Ber., 1992, 125, 1547; H. J. Breuning and S. Guelec, Z. Naturforsch., Teil B, 1986, 41, 1387; A. J. Ashe III and E. G. Ludwig, Jr., J. Organomet. Chem., 1986, 308, 289; W. W. du Mont, T. Severengiz and H. J. Breuning, Z. Naturforsch., Teil B, 1983, 38, 1306.
14. 2 (Z = S, Se, Te) are also known: R. S. Dickson and K. D. Heazle, J. Organomet. Chem., 1995, 493, 189; W. Uhl, M. Layh, G. Becker, K.-W. Klinkhammer and T. Hildenbrand, Chem. Ber., 1992, 125, 1547; H. J. Breuning and S. Guelec, Z. Naturforsch., Teil B, 1986, 41, 1387; A. J. Ashe III and E. G. Ludwig, Jr., J. Organomet. Chem., 1986, 308, 289; W. W. du Mont, T. Severengiz and H. J. Breuning, Z. Naturforsch., Teil B, 1983, 38, 1306.
15. 2 (Z = S, Se, Te) are also known: R. S. Dickson and K. D. Heazle, J. Organomet. Chem., 1995, 493, 189; W. Uhl, M. Layh, G. Becker, K.-W. Klinkhammer and T. Hildenbrand, Chem. Ber., 1992, 125, 1547; H. J. Breuning and S. Guelec, Z. Naturforsch., Teil B, 1986, 41, 1387; A. J. Ashe III and E. G. Ludwig, Jr., J. Organomet. Chem., 1986, 308, 289; W. W. du Mont, T. Severengiz and H. J. Breuning, Z. Naturforsch., Teil B, 1983, 38, 1306.
16. 2 (Z = S, Se, Te) are also known: R. S. Dickson and K. D. Heazle, J. Organomet. Chem., 1995, 493, 189; W. Uhl, M. Layh, G. Becker, K.-W. Klinkhammer and T. Hildenbrand, Chem. Ber., 1992, 125, 1547; H. J. Breuning and S. Guelec, Z. Naturforsch., Teil B, 1986, 41, 1387; A. J. Ashe III and E. G. Ludwig, Jr., J. Organomet. Chem., 1986, 308, 289; W. W. du Mont, T. Severengiz and H. J. Breuning, Z. Naturforsch., Teil B, 1983, 38, 1306.
17. 2 (Z = S, Se, Te) are also known: R. S. Dickson and K. D. Heazle, J. Organomet. Chem., 1995, 493, 189; W. Uhl, M. Layh, G. Becker, K.-W. Klinkhammer and T. Hildenbrand, Chem. Ber., 1992, 125, 1547; H. J. Breuning and S. Guelec, Z. Naturforsch., Teil B, 1986, 41, 1387; A. J. Ashe III and E. G. Ludwig, Jr., J. Organomet. Chem., 1986, 308, 289; W. W. du Mont, T. Severengiz and H. J. Breuning, Z. Naturforsch., Teil B, 1983, 38, 1306.
18. 2. Usually, mixing the two reagents in a flask placed about 2 m under a 40 W fluorescent lamp at room temperature for a few minutes leads to quantitative formation of the products. Only when the reactivity was low, was irradiation with a 200 W tungsten lamp performed.
19. 2 at 80 °C for 2 h in the dark.
20. 2Te was found to have occurred after prolonged irradiation (44 h) at room temperature.
21. W. Drenth, M. J. Janssen and G. J. M. van der Kerk, J. Organomet. Chem., 1964, 2, 265.
22. 2 to unsaturated carbon-carbon bonds under irradiation of visible light have been studied. For examples, see: A. Ogawa, I. Ogawa, R. Obayashi, K. Umezu, M. Doi and T. Hirao, J. Org. Chem., 1999, 64, 84; A. Ogawa, R. Obayashi, H. Ine, Y. Tsuboi, N. Sonoda and T. Hirao, J. Org. Chem., 1998, 63, 881; A. Ogawa, R. Obayashi, M. Doi, N. Sonoda and T. Hirao, J. Org. Chem., 1998, 63, 4277.
23. 2 to unsaturated carbon-carbon bonds under irradiation of visible light have been studied. For examples, see: A. Ogawa, I. Ogawa, R. Obayashi, K. Umezu, M. Doi and T. Hirao, J. Org. Chem., 1999, 64, 84; A. Ogawa, R. Obayashi, H. Ine, Y. Tsuboi, N. Sonoda and T. Hirao, J. Org. Chem., 1998, 63, 881; A. Ogawa, R. Obayashi, M. Doi, N. Sonoda and T. Hirao, J. Org. Chem., 1998, 63, 4277.
24. 2 to unsaturated carbon-carbon bonds under irradiation of visible light have been studied. For examples, see: A. Ogawa, I. Ogawa, R. Obayashi, K. Umezu, M. Doi and T. Hirao, J. Org. Chem., 1999, 64, 84; A. Ogawa, R. Obayashi, H. Ine, Y. Tsuboi, N. Sonoda and T. Hirao, J. Org. Chem., 1998, 63, 881; A. Ogawa, R. Obayashi, M. Doi, N. Sonoda and T. Hirao, J. Org. Chem., 1998, 63, 4277.
25. 2-initiated radical chain reactions; see D. P. Curran, M.-H. Chen and D. Kim, J. Am. Chem. Soc., 1989, 111, 6265.
26. 2. See ref. 11.
27. 6 at 80 °C in the dark in the presence of 10 mol% of AIBN led to 95% conversion after 2 h, whereas the same treatment in the absence of AIBN showed only 15% conversion.
28. 2, see: J. Spanswick and K. U. Ingold, Int. J. Chem. Kinet., 1970, 2, 157.
29. Note added at proof: We have found very recently that the December 20 issue of Chemical Abstracts has compiled a paper on a new method for the synthesis of stannyl selenides; see V. A. Potapov, S. V. Amosova, V. Svetlana, I. P. Beletskaya, A. A. Starkova, A. V. Martynov and L. Hevesi, Sulfur Lett., 1999, 22, 237; Chem. Abstr., 1999, 131, 337113u.
30. Note added at proof: We have found very recently that the December 20 issue of Chemical Abstracts has compiled a paper on a new method for the synthesis of stannyl selenides; see V. A. Potapov, S. V. Amosova, V. Svetlana, I. P. Beletskaya, A. A. Starkova, A. V. Martynov and L. Hevesi, Sulfur Lett., 1999, 22, 237; Chem. Abstr., 1999, 131, 337113u.