Synthesis and reactivity of subvalent compounds. Part 13: Reaction of triethyl orthoformate with amines and selenium - A convenient one-step three-component synthesis for selenoureas

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1295-1299

  Zhou, Yuehui ^b   Denk, Michael K ^a  

^a UNIVERSITY OF GUELPH   (Canada)

^b Cytec Canada Inc   (Canada)

Author keywords

Amine; Carbene; Enetetramines; Selenium; Selenoureas; Solvent free

Indexed keywords

AMINE; ETHYLENEDIAMINE DERIVATIVE; FORMIC ACID; INERT GAS; ISOPROPYLAMINE; N,N' DIMETHYLPROPYLENEDIAMINE; PIPERIDINE; SELENIUM DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; POLYMERIZATION; REACTION TIME; SYNTHESIS;

EID: 0037415486     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02818-6     Document Type: Article

References (84)

1. Kuhn N., Kratz T. Synthesis. 1993;561-562.
2. Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721.
3. Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721.
4. Hahn F.E., Wittenbecher L., Boese R., Bläser D. Chem. Eur. J. 5:1999;1931-1935.
5. For recent reviews, see: (a) Regitz, M. Angew. Chem. 1996, 108, 791-794; Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728; (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187; (b) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921; (c) Warkentin, J. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press: London, 1998; Vol. 2, p. 245; (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
6. For recent reviews, see: (a) Regitz, M. Angew. Chem. 1996, 108, 791-794; Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728; (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187; (b) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921; (c) Warkentin, J. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press: London, 1998; Vol. 2, p. 245; (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
7. For recent reviews, see: (a) Regitz, M. Angew. Chem. 1996, 108, 791-794; Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728; (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187; (b) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921; (c) Warkentin, J. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press: London, 1998; Vol. 2, p. 245; (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
8. For recent reviews, see: (a) Regitz, M. Angew. Chem. 1996, 108, 791-794; Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728; (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187; (b) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921; (c) Warkentin, J. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press: London, 1998; Vol. 2, p. 245; (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
9. For recent reviews, see: (a) Regitz, M. Angew. Chem. 1996, 108, 791-794; Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728; (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187; (b) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921; (c) Warkentin, J. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press: London, 1998; Vol. 2, p. 245; (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
10. For recent reviews, see: (a) Regitz, M. Angew. Chem. 1996, 108, 791-794; Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728; (b) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187; (b) Arduengo, A. J., III. Acc. Chem. Res. 1999, 32, 913-921; (c) Warkentin, J. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press: London, 1998; Vol. 2, p. 245; (d) Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
11. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
12. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
13. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
14. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
15. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
16. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
17. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
18. For reviews on tetraaminoethenes ('enetetramines'), see: (a) Wiberg, N. Angew. Chem. 1968, 80, 809; Angew. Chem., Int. Ed. Engl. 1968, 7, 766-779; (b) Hoffmann, R. W. Angew. Chem. 1968, 80, 823; Angew. Chem., Int. Ed. Engl. 1968, 7, 754-765. (c) Hocker, J.; Merten, R. Angew. Chem. 1972, 84, 1022; Angew. Chem., Int. Ed. Engl. 1972, 11, 964-973; (d) Haug, E.; Kantlehner, W. In Houben-Weyl, Methoden der Organischen Chemie, E15, 3, 2898-2931, Thieme Verlag: Stuttgart, 1993; (e) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
19. Denk M.K., Gupta S., Brownie J., Tajammul S., Lough A.J. Chem. Eur. J. 20:2001;4477-4486.
20. Denk M.K., Rodezno J. J. Organomet. Chem. 617-618:2001;737-740.
21. Denk M.K., Rodezno J. J. Organomet. Chem. 608:2000;122-125.
22. Denk M.K., Rodezno J., Gupta S., Lough A.J. J. Organomet. Chem. 617-618:2001;242-253.
23. Lehmann J.F., Urquhart S.G., Ennis L.E., Hitchcock A.P., Hatano K., Gupta S., Denk M.K. Organometallics. 18:1999;1862-1872.
24. Denk M.K., Hatano K., Ma M.J. Tetrahedron Lett. 40:1999;2057-2060 Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721.
25. Denk M.K., Hatano K., Ma M.J. Tetrahedron Lett. 40:1999;2057-2060 Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721.
26. Denk M.K., Hatano K., Ma M.J. Tetrahedron Lett. 40:1999;2057-2060 Denk, M. K.; Thadani, A.; Hatano, K.; Lough, A. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2607-2609; Angew. Chem. 1997, 109, 2719-2721.
27. Hitchcock A.P., Ennis L.E., Lehmann J.F., Denk M.K. J. El. Spec. 114:2001;1037-1041.
28. Leites L.A., Bukalov S.S., Denk M.K., West R., Haaf M. J. Mol. Struct. Theochem. 550:2000;329-335.
29. Denk M.K., Gupta S., Ramachandran R. Eur. J. Inorg. Chem. 1999;41-49.
30. Denk M.K., Hatano K., Lough A.J. Eur. J. Inorg. Chem. 1998;1067-1070.
31. Urquhart S., Hitchcock A.P., Denk M.K. Organometallics. 17:1998;2352-2360.
32. Denk M.K., Gupta S., Ramachandran R. Tetrahedron Lett. 37:1996;9025-9028.
33. Metzler N., Denk M.K. Chem. Commun. 1996;2657-2658.
34. Denk M., Lennon R., Hayashi R., West R., Haaland A., Belyakov A.V., Verne H.P., Wagner M., Metzler N. J. Am. Chem. Soc. 116:1994;2691-2692.
35. Denk M., Hayashi R.K., West R. J. Am. Chem. Soc. 116:1994;10813-10814.
36. Denk M., Green J.C., Metzler N., Wagner M. J. Chem. Soc., Dalton Trans. 1994;2405-2410.
37. Denk M., Hayashi R.K., West R. J. Chem. Soc., Chem. Commun. 1994;33-34.
38. 6).
39. For recent reviews on selenium compounds, see: (a) Murai, T.; Kato, S. Top. Curr. Chem. 2000, 208, 177-199; (b) The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons, 1987; Vol. 2; (c) Nishibayashi, Y.; Uemura, S. Top. Curr. Chem. 2000, 208, 235-255; (d) Wirth, T. Tetrahedron 1999, 55, 1-28. (Tetrahedron Report Nr. 47).
40. For recent reviews on selenium compounds, see: (a) Murai, T.; Kato, S. Top. Curr. Chem. 2000, 208, 177-199; (b) The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons, 1987; Vol. 2; (c) Nishibayashi, Y.; Uemura, S. Top. Curr. Chem. 2000, 208, 235-255; (d) Wirth, T. Tetrahedron 1999, 55, 1-28. (Tetrahedron Report Nr. 47).
41. For recent reviews on selenium compounds, see: (a) Murai, T.; Kato, S. Top. Curr. Chem. 2000, 208, 177-199; (b) The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons, 1987; Vol. 2; (c) Nishibayashi, Y.; Uemura, S. Top. Curr. Chem. 2000, 208, 235-255; (d) Wirth, T. Tetrahedron 1999, 55, 1-28. (Tetrahedron Report Nr. 47).
42. For recent reviews on selenium compounds, see: (a) Murai, T.; Kato, S. Top. Curr. Chem. 2000, 208, 177-199; (b) The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons, 1987; Vol. 2; (c) Nishibayashi, Y.; Uemura, S. Top. Curr. Chem. 2000, 208, 235-255; (d) Wirth, T. Tetrahedron 1999, 55, 1-28. (Tetrahedron Report Nr. 47).
43. For the synthesis of selenium-heterocycles from selenoureas, see: (a) Weber, M.; Hartmann, H. Z. Chem. 1987, 27, 95-96; (b) Comrie, A. M. J. Chem. Soc. 1963, 5713-5717; (c) Günther, W. H. H.; Searle, R.; Sieber, F. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 417-424; (d) Arca, M.; Demartin, F.; Devillanova, F. A.; Isaia, F.; Lelj, F.; Lippolis, V.; Verani, G. Can. J. Chem. 2000, 78, 1147-1157.
44. For the synthesis of selenium-heterocycles from selenoureas, see: (a) Weber, M.; Hartmann, H. Z. Chem. 1987, 27, 95-96; (b) Comrie, A. M. J. Chem. Soc. 1963, 5713-5717; (c) Günther, W. H. H.; Searle, R.; Sieber, F. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 417-424; (d) Arca, M.; Demartin, F.; Devillanova, F. A.; Isaia, F.; Lelj, F.; Lippolis, V.; Verani, G. Can. J. Chem. 2000, 78, 1147-1157.
45. For the synthesis of selenium-heterocycles from selenoureas, see: (a) Weber, M.; Hartmann, H. Z. Chem. 1987, 27, 95-96; (b) Comrie, A. M. J. Chem. Soc. 1963, 5713-5717; (c) Günther, W. H. H.; Searle, R.; Sieber, F. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 417-424; (d) Arca, M.; Demartin, F.; Devillanova, F. A.; Isaia, F.; Lelj, F.; Lippolis, V.; Verani, G. Can. J. Chem. 2000, 78, 1147-1157.
46. For the synthesis of selenium-heterocycles from selenoureas, see: (a) Weber, M.; Hartmann, H. Z. Chem. 1987, 27, 95-96; (b) Comrie, A. M. J. Chem. Soc. 1963, 5713-5717; (c) Günther, W. H. H.; Searle, R.; Sieber, F. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 417-424; (d) Arca, M.; Demartin, F.; Devillanova, F. A.; Isaia, F.; Lelj, F.; Lippolis, V.; Verani, G. Can. J. Chem. 2000, 78, 1147-1157.
47. For the use of selenoureas as building blocks for organic conductors, see: (a) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A; Trogu, E. F. Gazz. Chim. Ital. 1994, 124, 445-454; (b) Bigoli, F.; Dematin, F.; Deplano, P.; Devillanova, F. A.; Isaia, A. F.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 3194-3201; (c) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 5403-5406; (d) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Synth. Met. 1997, 86, 1853-1854; (e) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Eur. J. Inorg. Chem. 1998, 137-141; (f) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Mater. Chem. 1998, 8, 1145-1150; (g) Boyle, P. D.; Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Pritchard, R. G.; Teat, S. J. J. Chem. Soc., Dalton Trans. 1999, 2845-2852.
48. For the use of selenoureas as building blocks for organic conductors, see: (a) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A; Trogu, E. F. Gazz. Chim. Ital. 1994, 124, 445-454; (b) Bigoli, F.; Dematin, F.; Deplano, P.; Devillanova, F. A.; Isaia, A. F.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 3194-3201; (c) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 5403-5406; (d) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Synth. Met. 1997, 86, 1853-1854; (e) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Eur. J. Inorg. Chem. 1998, 137-141; (f) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Mater. Chem. 1998, 8, 1145-1150; (g) Boyle, P. D.; Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Pritchard, R. G.; Teat, S. J. J. Chem. Soc., Dalton Trans. 1999, 2845-2852.
49. For the use of selenoureas as building blocks for organic conductors, see: (a) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A; Trogu, E. F. Gazz. Chim. Ital. 1994, 124, 445-454; (b) Bigoli, F.; Dematin, F.; Deplano, P.; Devillanova, F. A.; Isaia, A. F.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 3194-3201; (c) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 5403-5406; (d) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Synth. Met. 1997, 86, 1853-1854; (e) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Eur. J. Inorg. Chem. 1998, 137-141; (f) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Mater. Chem. 1998, 8, 1145-1150; (g) Boyle, P. D.; Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Pritchard, R. G.; Teat, S. J. J. Chem. Soc., Dalton Trans. 1999, 2845-2852.
50. For the use of selenoureas as building blocks for organic conductors, see: (a) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A; Trogu, E. F. Gazz. Chim. Ital. 1994, 124, 445-454; (b) Bigoli, F.; Dematin, F.; Deplano, P.; Devillanova, F. A.; Isaia, A. F.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 3194-3201; (c) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 5403-5406; (d) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Synth. Met. 1997, 86, 1853-1854; (e) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Eur. J. Inorg. Chem. 1998, 137-141; (f) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Mater. Chem. 1998, 8, 1145-1150; (g) Boyle, P. D.; Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Pritchard, R. G.; Teat, S. J. J. Chem. Soc., Dalton Trans. 1999, 2845-2852.
51. For the use of selenoureas as building blocks for organic conductors, see: (a) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A; Trogu, E. F. Gazz. Chim. Ital. 1994, 124, 445-454; (b) Bigoli, F.; Dematin, F.; Deplano, P.; Devillanova, F. A.; Isaia, A. F.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 3194-3201; (c) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 5403-5406; (d) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Synth. Met. 1997, 86, 1853-1854; (e) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Eur. J. Inorg. Chem. 1998, 137-141; (f) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Mater. Chem. 1998, 8, 1145-1150; (g) Boyle, P. D.; Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Pritchard, R. G.; Teat, S. J. J. Chem. Soc., Dalton Trans. 1999, 2845-2852.
52. For the use of selenoureas as building blocks for organic conductors, see: (a) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A; Trogu, E. F. Gazz. Chim. Ital. 1994, 124, 445-454; (b) Bigoli, F.; Dematin, F.; Deplano, P.; Devillanova, F. A.; Isaia, A. F.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 3194-3201; (c) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 5403-5406; (d) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Synth. Met. 1997, 86, 1853-1854; (e) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Eur. J. Inorg. Chem. 1998, 137-141; (f) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Mater. Chem. 1998, 8, 1145-1150; (g) Boyle, P. D.; Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Pritchard, R. G.; Teat, S. J. J. Chem. Soc., Dalton Trans. 1999, 2845-2852.
53. For the use of selenoureas as building blocks for organic conductors, see: (a) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A; Trogu, E. F. Gazz. Chim. Ital. 1994, 124, 445-454; (b) Bigoli, F.; Dematin, F.; Deplano, P.; Devillanova, F. A.; Isaia, A. F.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 3194-3201; (c) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Inorg. Chem. 1996, 35, 5403-5406; (d) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Synth. Met. 1997, 86, 1853-1854; (e) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. Eur. J. Inorg. Chem. 1998, 137-141; (f) Bigoli, F.; Deplano, P.; Devillanova, F. A.; Girlando, A.; Lippolis, V.; Mercuri, M. L.; Pellinghelli, M. A.; Trogu, E. F. J. Mater. Chem. 1998, 8, 1145-1150; (g) Boyle, P. D.; Cross, W. I.; Godfrey, S. M.; McAuliffe, C. A.; Pritchard, R. G.; Teat, S. J. J. Chem. Soc., Dalton Trans. 1999, 2845-2852.
54. Hope H. Acta Chem. Scand. 18:1964;1800-1800.
55. Guziec F.S. Patai S. The Chemistry of Organic Selenium and Tellurium Compounds. 2:1987;255 John Wiley & Sons.
56. Grimm H.G., Metzger H. Chem. Ber. 69:1936;1356-1364.
57. Warner J.S. J. Org. Chem. 28:1963;1642-1644.
58. Rosenbaum A. J. Prakt. Chem. 37:1968;200-205.
59. Henriksen L. Synthesis. 9:1982;773-776.
60. Pan W.H., Fackler J.P. Jr. Inorg. Synth. 21:1985;6-11.
61. Takikawa Y., Watanabe H., Sasaki R., Shimada K. Bull. Chem. Soc. Jpn. 67:1994;876-878.
62. Jensen K.A., Nielsen P.H. Acta Chem. Scand. 20:1966;597-629.
63. Zhou Y.H., Linden A., Heimgartner H. Helv. Chim. Acta. 83:2000;1576-1598.
64. Review: Petrov M.L., Zmitrovich N.I. Russ. J. Gen. Chem. 69:1999;245-256.
65. Wood P.T., Woollins J.D. Phosphorus, Sulfur Silicon Relat. Elem. 41:1989;51-56.
66. Fitzmaurice J.C., Williams D.J., Wood P.T., Woollins J.D. J. Chem. Soc., Chem. Commun. 11:1988;741-743.
67. Jensen K.A., Felbert G., Kägi B. Acta Chem. Scand. 20:1966;281-282.
68. Shimada K., Jin N., Kawaguchi M., Dobashi K., Nagano Y., Fujimura M., Kudoh E., Kai T., Saito N., Masuda J., Iwaya M., Fujiisawa H., Aoyagi S., Takikawa Y. Bull. Chem. Soc. Jpn. 70:1997;197-206.
69. Yoshifuji M., Higeta N., An D.-L., Toyota K. Chem. Lett. 1998;17-18.
70. Michael J.P., Reid D.H., Rose B.G., Speirs R.A. J. Chem. Soc., Chem. Commun. 1988;1494-1496.
71. Segi M., Koyama T., Nakajima T., Suga S., Murai S., Sonoda N. Tetrahedron Lett. 30:1989;2095-2097.
72. Kuhn N., Henkel G., Kratz T. Z. Naturforsch. B. 48:1993;973-977.
73. Williams D.J., Fawcett-Brown M.R., Raye R.R., Vanderveer D., Pang Y.T., Jones R.L., Bergbauer K.L. Heteroatom Chem. 4:1993;409-414.
74. Schönberg A., Singer E., Stephan W. Chem. Ber. 116:1983;2068-2073.
75. An early example for the chemical cleavage of electron rich olefins by sulfur was described by A. Schönberg in 1925: Schönberg, A.; Rosenbach, A.; Krüll, H.; Ostwaldt, U. Ber. Dtsch. Chem. Ges. 1925, 58, 1793-1801; Schönberg, A.; Asker, W. J. Chem. Soc. (London) 1942, 272-274. For an excellent account of Schönberg's research see the obituary by Singer: Singer, E. Chem. Ber. 1987, 120, I-XIX. For early research on stabilized carbenes see the obituary for H. Scheibler: Wanzlick, H.-W. Chem. Ber. 1969, 102, XVII-XXXIX.
76. Wanzlick H.-W., Lachmann B., Schikora E. Chem. Ber. 98:1965;3170-3177.
77. Wanzlick, H.-W.; Esser, F.; Kleiner, H.-J. Chem. Ber. 1963, 96, 1208-1212. For the formation of enetetramines from DMF acetals and 1,2-diaminoethanes see: Çetinkaya, B.; Çetinkaya, E.; Chamizo, J. A.; Hitchcock, P. B.; Jasim, H. A.; Kücükbay, H.; Lappert, M. F. J. Chem. Soc., Perkin Trans. 1 1998, 2047-2054.
78. Wanzlick, H.-W.; Esser, F.; Kleiner, H.-J. Chem. Ber. 1963, 96, 1208-1212. For the formation of enetetramines from DMF acetals and 1,2-diaminoethanes see: Çetinkaya, B.; Çetinkaya, E.; Chamizo, J. A.; Hitchcock, P. B.; Jasim, H. A.; Kücükbay, H.; Lappert, M. F. J. Chem. Soc., Perkin Trans. 1 1998, 2047-2054.
79. Schönberg A., Singer E., Stephan W. Chem. Ber. 120:1987;1581-1588.
80. Kantlehner W., Hauber M., Vettel M. J. Prakt. Chem. Chem. Z. 338:1996;403-413.
81. Maas G., Singer B. Chem. Ber. 116:1983;3659-3674.
82. Cetinkaya B., Cetinkaya E., Kucukbay H., Durmaz R. Arzneim. Forsch. 46:1996;1154-1158.
83. Shimada K., Yamaguchi M., Sasaki T., Ohnishi K., Takikawa Y. Bull. Chem. Soc. Jpn. 69:1996;2235-2242.
84. -1 was calculated for the isomerization of imidazole-2-ylidene to imidazole: Maier G., Endres J. Eur. J. Org. Chem. 1998;1517-1520.