Reaction of Selenoic Acid O-Methyl Esters with Aluminum Thiolates Leading to Aromatic Selenothioic Acid S-Alkyl Esters and Their Characterization

Journal of Organic Chemistry

Volumn 60, Issue 9, 1995, Pages 2942-2945

  Murai, Toshiaki ^a   Ogino, Yuji ^a   Mizutani, Tomoyoshi ^a   Kanda, Takahiro ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007684213     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00114a058     Document Type: Article

References (62)

1. For selenoaldehydes: Kirby, G. W.; Trethewey, A. N. J. Chem. Soc, Perkin Trans. 1 1988, 1913.
2. Meinke, P. T.; Krafft, G. A. J. Am. Chem. Soc. 1988, 110, 8671.
3. Erker, G.; Hock, R.; Nolte, R. J. Am. Chem. Soc. 1988, 110, 624.
4. Segi, M.; Nakajima, T.; Suga, S.; Murari, S.; Ryu, I.; Ogawa, A.; Sonoda, N. J. Am. Chem. Soc. 1988, 110, 1976.
5. Okazaki, R.; Kumon, N.; Inamoto, N. J. Am. Chem. Soc. 1989, 111, 5949.
6. Takikawa, Y.; Uwano, A.; Watanabe, H.; Asanuma, M.; Shimada, K. Tetrahedron Lett. 1989, 30, 6047.
7. Okuma, K.; Komiya, Y.; Kaneko, I.; Tachibana, Y.; Iwata, E.; Ohta, H. Bull. Chem. Soc. Jpn. 1990, 63, 1653.
8. Segi, M.; Kato, M.; Nakajima, T. Tetrahedron Lett. 1991, 32, 7427.
9. Li, G. M.; Segi, M.; Nakajima, T. Tetrahedron Lett. 1992, 33, 3515.
10. Duchenet, V.; Vallée, Y. Tetra hedron Lett. 1993, 34, 4925.
11. For selenoketones: Ishii, A.; Okazaki, R.; Inamoto, N. Bull. Chem. Soc. Jpn. 1988, 61, 861.
12. Meinke, P. T.; Krafft, G. A. J. Am. Chem. Soc. 1988, 110, 8679.
13. Segi, M.; Koyama, T.; Nakajima, T.; Suga, S.; Murai, S.; Sonoda, N. Tetrahedron Lett. 1989, 30, 2095.
14. Erker, G.; Hock, R.; Krüger, C.; Werner, S.; Klarner, F.-G.; Artschwa-ger-Perl, U. Angew. Chem., Int. Ed. Engl. 1990, 29, 1067.
15. Okuma, K.; Kojima, K.; Kaneko, I.; Ohta, H. Chem. Lett. 1991, 1053.
16. Okuma, K.; Kojima, K.; Kaneko, I.; Ohta, H. Tetrahedron Lett. 1992, 33, 1333.
17. Shimada, K.; Jin, N.; Fujimura, M.; Nagano, Y.; Kudoh, E.; Takikawa, Y. Chem. Lett. 1992, 1843.
18. Ishii, A.; Ding, M.-X.; Nakayama, J.; Hoshino, M. Chem. Lett. 1992, 2289.
19. Brooks, P. R.; Bishop, R.; Craig, D. C.; Scudder, M. L. J. Org. Chem. 1993, 58, 5900.
20. Ding, M.-X.; Ishii, A.; Nakayama, J.; Hoshino, M. Bull. Chem. Soc. Jpn. 1993, 66, 1714.
21. Okuma, K.; Kojima, K.; Kaneko, I.; Tsujimoto, Y.; Ohta, H.; Yokomori, Y. J. Chem. Soc, Perkin Trans. 1 1994, 2151.
22. Reviews: Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Baldwin, J. E., Ed.; Pergamon Press: New York, 1986; p 58.
23. Guziec, F. S., Jr. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1987; p 215.
24. Guziec, F. S., Jr. In Organoselenium Chemistry; Liotta, D., Ed.; Wiley-Interscience: New York, 1987; Vol. 2, p 277.
25. Okazaki, R. J. Synth. Org. Chem., Jpn. 1988, 46, 1149.
26. Jensen, K. A.; Mygind, H.; Nielsen, P. H. In Organic Selenium Compounds: Their Chemistry and Biology; Klayman, D. L., Giinther, W. H. H., Eds.; Wiley-Interscience: New York, 1973; p 263.
27. Kato, S.; Murai, T.; Ishida, M. Org. Prep. Proced. Int. 1986, 18, 369.
28. Collard-Charon, C.; Renson, M. Bull. Soc. Chim. Belg. 1962, 71, 563.
29. For recent reports of the synthesis of selenoesters: Ishihara, H.; Yoshimi, M.; Kara, N.; Ando, H.; Kato, S. Bull. Chem. Soc. Jpn. 1990, 63, 835.
30. Segi, M.; Takahashi, H.; Ichinose, H.; Li, G. M.; Nakajima, T. Tetrahedron Lett. 1992, 33, 7865.
31. Ogawa, A.; Sonoda, N. In Comprehensive Organic Syntheses; Trost, B. M., Fleming, 1., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, Chapter 2.6.
32. Wright, S. W. Tetrahedron Lett. 1994, 35, 1331.
33. For reviews of dithioic acid esters, see: Scheithauer, S.; Mayer, R. In Topics in Surfur Chemistry; Senning, A., Ed.; George Thieme Publishers: Stuttgart, 1979; Vol. 4.
34. Ramadas, S. R.; Srinivasan, P. S.; Ramachandran, J.; Sastry, V. V. S. K. Synthesis 1983, 605.
35. Kato, S.; Ishida, M. Sulfur Rep. 1988, 8, 155.
36. Kato, S.; Murai, T. In Supplement B: The Chemistry of Acid Derivatives; Patai, 5., Ed.; John Wiley & Sons: New York, 1992; Vol. 2, p 803.
37. Metzner, P. Synthesis 1992, 1185.
38. For the syntheses of selenothioic acid Se-esters: Renson, M.; Collinene, R. Bull. Soc. Chim. Belg. 1964, 73, 491.
39. Chu, S. H.; Mautner, H. G. J. Med. Chem. 1970, 13, 214.
40. Raash, M. H. J. Org. Chem. 1972, 37, 1347.
41. Kato, S.; Yasui, E.; Terashima, K.; Ishihara, H.; Murai, T. Bull. Chem. Soc. Jpn. 1988, 61, 3931.
42. Kato, S.; Fukushima, T.; Ishihara, H.; Murai, T. Bull. Chem. Soc. Jpn. 1990, 63, 638.
43. Kato, S.; Masumoto, S.; Ikeda, S.; Itoh, M.; Murai, T.; Kato, S. Z. Chem. 1990, 30, 67.
44. Khalid, M.; Ripoll, J.-L.; Vallée, Y. J. Chem. Soc., Chem. Commun. 1991, 964.
45. Lemarié, M.; Vallée, Y.; Worrell, M. Tetrahedron Lett. 1992, 33, 6131.
46. Choi, K. S.; Akiyama, I.; Hoshino, M.; Nakayama, J. Bull. Chem. Soc. Jpn. 1993, 66, 623.
47. Murai, T.; Mizutani, T.; Kanda, T.; Kato, S. J. Am. Chem. Soc. 1993, 115, 5823.
48. Murai, T.; Mizutani, T.; Kanda, T.; Kato, S. Heteroatom Chemistry, in press.
49. Kato, S.; Komuro, T.; Kanda, T.; Ishihara, H.; Murai, T. J. Am. Chem. Soc. 1993, 115, 3000.
50. Murai, T.; Hayashi, A.; Kanda, T.; Kato, S. Chem. Lett. 1993, 1469.
51. Murai, T.; Takada, H.; Kanda, T.; Kato, S. Tetrahedron Lett. 1994, 35, 8817.
52. Aluminum methanethiolate was prepared in a manner similar to that of aluminum methaneselenolate: Kozikowski, A. P.; Ames, A. J. Org. Chem. 1978, 43, 2735.
53. Sviridov, A. F.; Ermolenko, M. S.; Yashunsky, D. V.; Kochetkov, N. K. Tetrahedron Lett. 1983, 24, 4355.
54. Kozikowski, A. P.; Ames, A. Tetrahedron 1985, 41, 4821.
55. Corey, E. J.; Beams, D. J. J. Am. Chem. Soc. 1973, 95, 5829.
56. Warwell, S.; Ahlfaenger, B. Chem.-Ztg. 1977, 101, 103.
57. Hatch, R. P.; Weinreb, S. M. J. Org. Chem. 1977, 42, 3960.
58. Cohen, T.; Gapinski, R. E. Tetrahedron Lett. 1978, 4319.
59. Inoue, T.; Takeda, T.; Kambe, N.; Ogawa, A.; Ryu, I.; Sonoda, N. J. Org. Chem. 1994, 59, 5824.
60. Cohen, V. I. J. Org. Chem. 1977, 42, 2645.
61. Cullen, E. R.; Guziec, F. S., Jr.; Murphy, C. J.; Wong, T. C.; Andersen, K. K. J. Am. Chem. Soc. 1981, 103, 7055.
62. Luthra, N. P.; Odom, J. D. In The Chemistry of Organic Selenium and Tellurium Compounds, Patai, S., Ed.; John Wiley & Sons: New York, 1986; Vol. 1, p 189.