Novel photochemical ring contraction of 1,4,7,10-tetraisopropyldibenzo[c,g][1,2,5,6]tetrachalcogenocins: Efficient synthesis, structure, and redox reactions of 1,4,6,9-tetraisopropylchalcogenanthrenes

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 9101-9106

  Ogawa, Satoshi ^a   Sugawara, Mutsumi ^a   Kawai, Yasushi ^b   Niizuma, Shigeya ^a   Kimura, Takeshi ^a   Sato, Ryu ^a  

^a IWATE UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Electron transfer; Photochemistry; Selenium heterocycles; Sulfur heterocycles; X ray crystal structures

Indexed keywords

CHALCOGEN; CYCLIC SULFIDE; SELENIUM DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; ION CURRENT; IRRADIATION; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033579592     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01931-0     Document Type: Article

References (34)

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10. Dougherty, G.; Hammond, P. D. J. Am. Chem. Soc. 1935, 57, 117-118; Nakanishi, W.; Ikeda, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1651-1664; Nakayama, J.; Kashiwagi, M.; Yomoda, R.; Hoshino, M. Nippon Kagaku Kaishi 1987, 1424-1429; Engman, L.; Hellberg, J.; Ishag, C.; Söderholm, S. J. Chem. Soc., Perkin Trans. 1 1988, 2095-2101 ; Furukawa, N.; Kimura, T.; Horie, Y; Ogawa, S. Heterocycles 1991, 32, 675-678; Dötze, M.; Klar, G. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 84, 95-106; Engman, L.; Eriksson, P. Heterocycles 1996, 43, 861-871.
11. Dougherty, G.; Hammond, P. D. J. Am. Chem. Soc. 1935, 57, 117-118; Nakanishi, W.; Ikeda, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1651-1664; Nakayama, J.; Kashiwagi, M.; Yomoda, R.; Hoshino, M. Nippon Kagaku Kaishi 1987, 1424-1429; Engman, L.; Hellberg, J.; Ishag, C.; Söderholm, S. J. Chem. Soc., Perkin Trans. 1 1988, 2095-2101 ; Furukawa, N.; Kimura, T.; Horie, Y; Ogawa, S. Heterocycles 1991, 32, 675-678; Dötze, M.; Klar, G. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 84, 95-106; Engman, L.; Eriksson, P. Heterocycles 1996, 43, 861-871.
12. Dougherty, G.; Hammond, P. D. J. Am. Chem. Soc. 1935, 57, 117-118; Nakanishi, W.; Ikeda, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1651-1664; Nakayama, J.; Kashiwagi, M.; Yomoda, R.; Hoshino, M. Nippon Kagaku Kaishi 1987, 1424-1429; Engman, L.; Hellberg, J.; Ishag, C.; Söderholm, S. J. Chem. Soc., Perkin Trans. 1 1988, 2095-2101 ; Furukawa, N.; Kimura, T.; Horie, Y; Ogawa, S. Heterocycles 1991, 32, 675-678; Dötze, M.; Klar, G. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 84, 95-106; Engman, L.; Eriksson, P. Heterocycles 1996, 43, 861-871.
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15. Ogawa, S.; Kikuchi, T.; Sasaki, A.; Chida, S.; Sato, R. Tetrahedron Lett. 1994, 35, 5469-5472.
16. w=0.081. Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre (CCDC).
17. Setzer, W. N.; Glass, R. S. In Conformational Analysis of Medium-sized Heterocycles; Glass, R. S., Ed. Conformational analysis of medium-sized sulfur-containing heterocycles. VCH Publishers: New York, 1988; pp. 151-180. For recent examples, see: Lakshmikantham, M. V.; Raasch, M. S.; Cava, M. P.; Bott, S. G.; Atwood, J. L. J. Org. Chem. 1987, 52, 1874-1877; Yang, X.; Rauchfuss, T. B.; Wilson, S. J. Chem. Soc., Chem. Commun. 1990, 34-36; Borisenko, K. B.; Broschag, M.; Hargittai, I.; Klapötke, T. M.; Schröder, D.; Schulz, A.; Schwarz, H.; Tornieporth-Oetting, I. C.; White, P. S. J. Chem. Soc., Dalton Trans. 1994, 2705-2712; Shimizu, T; Iwata, K.; Kamigata, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 2357-2359.
18. Setzer, W. N.; Glass, R. S. In Conformational Analysis of Medium-sized Heterocycles; Glass, R. S., Ed. Conformational analysis of medium-sized sulfur-containing heterocycles. VCH Publishers: New York, 1988; pp. 151-180. For recent examples, see: Lakshmikantham, M. V.; Raasch, M. S.; Cava, M. P.; Bott, S. G.; Atwood, J. L. J. Org. Chem. 1987, 52, 1874-1877; Yang, X.; Rauchfuss, T. B.; Wilson, S. J. Chem. Soc., Chem. Commun. 1990, 34-36; Borisenko, K. B.; Broschag, M.; Hargittai, I.; Klapötke, T. M.; Schröder, D.; Schulz, A.; Schwarz, H.; Tornieporth-Oetting, I. C.; White, P. S. J. Chem. Soc., Dalton Trans. 1994, 2705-2712; Shimizu, T; Iwata, K.; Kamigata, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 2357-2359.
19. Setzer, W. N.; Glass, R. S. In Conformational Analysis of Medium-sized Heterocycles; Glass, R. S., Ed. Conformational analysis of medium-sized sulfur-containing heterocycles. VCH Publishers: New York, 1988; pp. 151-180. For recent examples, see: Lakshmikantham, M. V.; Raasch, M. S.; Cava, M. P.; Bott, S. G.; Atwood, J. L. J. Org. Chem. 1987, 52, 1874-1877; Yang, X.; Rauchfuss, T. B.; Wilson, S. J. Chem. Soc., Chem. Commun. 1990, 34-36; Borisenko, K. B.; Broschag, M.; Hargittai, I.; Klapötke, T. M.; Schröder, D.; Schulz, A.; Schwarz, H.; Tornieporth-Oetting, I. C.; White, P. S. J. Chem. Soc., Dalton Trans. 1994, 2705-2712; Shimizu, T; Iwata, K.; Kamigata, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 2357-2359.
20. Setzer, W. N.; Glass, R. S. In Conformational Analysis of Medium-sized Heterocycles; Glass, R. S., Ed. Conformational analysis of medium-sized sulfur-containing heterocycles. VCH Publishers: New York, 1988; pp. 151-180. For recent examples, see: Lakshmikantham, M. V.; Raasch, M. S.; Cava, M. P.; Bott, S. G.; Atwood, J. L. J. Org. Chem. 1987, 52, 1874-1877; Yang, X.; Rauchfuss, T. B.; Wilson, S. J. Chem. Soc., Chem. Commun. 1990, 34-36; Borisenko, K. B.; Broschag, M.; Hargittai, I.; Klapötke, T. M.; Schröder, D.; Schulz, A.; Schwarz, H.; Tornieporth-Oetting, I. C.; White, P. S. J. Chem. Soc., Dalton Trans. 1994, 2705-2712; Shimizu, T; Iwata, K.; Kamigata, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 2357-2359.
21. Setzer, W. N.; Glass, R. S. In Conformational Analysis of Medium-sized Heterocycles; Glass, R. S., Ed. Conformational analysis of medium-sized sulfur-containing heterocycles. VCH Publishers: New York, 1988; pp. 151-180. For recent examples, see: Lakshmikantham, M. V.; Raasch, M. S.; Cava, M. P.; Bott, S. G.; Atwood, J. L. J. Org. Chem. 1987, 52, 1874-1877; Yang, X.; Rauchfuss, T. B.; Wilson, S. J. Chem. Soc., Chem. Commun. 1990, 34-36; Borisenko, K. B.; Broschag, M.; Hargittai, I.; Klapötke, T. M.; Schröder, D.; Schulz, A.; Schwarz, H.; Tornieporth-Oetting, I. C.; White, P. S. J. Chem. Soc., Dalton Trans. 1994, 2705-2712; Shimizu, T; Iwata, K.; Kamigata, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 2357-2359.
22. -1 4800); 2b, 263 (13400) and 322 (4600); 2c, 317 (3700); 2d, 255 (26700) and 319 (7500).
23. Very recently, similar photochemical reactions of tetrathiocins have been reported, see: Chivers, T.; Parvez, M.; Vargas- Baca, I.; Schatte, G. Can. J. Chem. 1998, 76, 1092-1101.
24. w=0.069. Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre (CCDC).
25. Hargittai, I.; Rozsondai, B. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S.; Rappoport, Z., Eds. Structural chemistry of organic compounds containing selenium or tellurium. John Wiley and Sons: New York, 1986; Vol. 1, pp. 63-155.
26. -1.
27. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372; Bandlish, B. K.; Shine, H. J. ibid. 1977, 42, 561-563; Boduszek, B.; Shine, H. J. ibid. 1988, 53, 5142-5143; Bock, H.; Pittmeyer, P. Phosphorous, Sulfur Silicon Relat. Elem. 1992, 68, 261-291; Bock, H.; Rauschenbach, A.; Näther, C; Kleine, M.; Havlas, Z. Chem. Ber. 1994, 127, 2043-2049; Zhao, W.; Shine, H. J.; Whittlesey, B. R. J. Org. Chem. 1997, 62, 8693-8701; Doménech, A.; Casades, I.; Garía, H. ibid. 1999, 64, 3731-3735.
28. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372; Bandlish, B. K.; Shine, H. J. ibid. 1977, 42, 561-563; Boduszek, B.; Shine, H. J. ibid. 1988, 53, 5142-5143; Bock, H.; Pittmeyer, P. Phosphorous, Sulfur Silicon Relat. Elem. 1992, 68, 261-291; Bock, H.; Rauschenbach, A.; Näther, C; Kleine, M.; Havlas, Z. Chem. Ber. 1994, 127, 2043-2049; Zhao, W.; Shine, H. J.; Whittlesey, B. R. J. Org. Chem. 1997, 62, 8693-8701; Doménech, A.; Casades, I.; Garía, H. ibid. 1999, 64, 3731-3735.
29. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372; Bandlish, B. K.; Shine, H. J. ibid. 1977, 42, 561-563; Boduszek, B.; Shine, H. J. ibid. 1988, 53, 5142-5143; Bock, H.; Pittmeyer, P. Phosphorous, Sulfur Silicon Relat. Elem. 1992, 68, 261-291; Bock, H.; Rauschenbach, A.; Näther, C; Kleine, M.; Havlas, Z. Chem. Ber. 1994, 127, 2043-2049; Zhao, W.; Shine, H. J.; Whittlesey, B. R. J. Org. Chem. 1997, 62, 8693-8701; Doménech, A.; Casades, I.; Garía, H. ibid. 1999, 64, 3731-3735.
30. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372; Bandlish, B. K.; Shine, H. J. ibid. 1977, 42, 561-563; Boduszek, B.; Shine, H. J. ibid. 1988, 53, 5142-5143; Bock, H.; Pittmeyer, P. Phosphorous, Sulfur Silicon Relat. Elem. 1992, 68, 261-291; Bock, H.; Rauschenbach, A.; Näther, C; Kleine, M.; Havlas, Z. Chem. Ber. 1994, 127, 2043-2049; Zhao, W.; Shine, H. J.; Whittlesey, B. R. J. Org. Chem. 1997, 62, 8693-8701; Doménech, A.; Casades, I.; Garía, H. ibid. 1999, 64, 3731-3735.
31. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372; Bandlish, B. K.; Shine, H. J. ibid. 1977, 42, 561-563; Boduszek, B.; Shine, H. J. ibid. 1988, 53, 5142-5143; Bock, H.; Pittmeyer, P. Phosphorous, Sulfur Silicon Relat. Elem. 1992, 68, 261-291; Bock, H.; Rauschenbach, A.; Näther, C; Kleine, M.; Havlas, Z. Chem. Ber. 1994, 127, 2043-2049; Zhao, W.; Shine, H. J.; Whittlesey, B. R. J. Org. Chem. 1997, 62, 8693-8701; Doménech, A.; Casades, I.; Garía, H. ibid. 1999, 64, 3731-3735.
32. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372; Bandlish, B. K.; Shine, H. J. ibid. 1977, 42, 561-563; Boduszek, B.; Shine, H. J. ibid. 1988, 53, 5142-5143; Bock, H.; Pittmeyer, P. Phosphorous, Sulfur Silicon Relat. Elem. 1992, 68, 261-291; Bock, H.; Rauschenbach, A.; Näther, C; Kleine, M.; Havlas, Z. Chem. Ber. 1994, 127, 2043-2049; Zhao, W.; Shine, H. J.; Whittlesey, B. R. J. Org. Chem. 1997, 62, 8693-8701; Doménech, A.; Casades, I.; Garía, H. ibid. 1999, 64, 3731-3735.
33. Murata, Y.; Shine, H. J. J. Org. Chem. 1969, 34, 3368-3372; Bandlish, B. K.; Shine, H. J. ibid. 1977, 42, 561-563; Boduszek, B.; Shine, H. J. ibid. 1988, 53, 5142-5143; Bock, H.; Pittmeyer, P. Phosphorous, Sulfur Silicon Relat. Elem. 1992, 68, 261-291; Bock, H.; Rauschenbach, A.; Näther, C; Kleine, M.; Havlas, Z. Chem. Ber. 1994, 127, 2043-2049; Zhao, W.; Shine, H. J.; Whittlesey, B. R. J. Org. Chem. 1997, 62, 8693-8701; Doménech, A.; Casades, I.; Garía, H. ibid. 1999, 64, 3731-3735.
34. 6: C, 46.24, H, 5.17. Found: C, 45.88, H, 5.37%. We have so far been unable to obtain radical cation salt (4c) from thiaselenanthrene (3c) suitable for elemental analysis due to its inherent instability.