Selenotellurocarbamic acid Te-alkyl esters: First isolation and characterization

Organometallics

Volumn 15, Issue 26, 1996, Pages 5753-5755

  Kanda, Takahiro ^a   Aoki, Hiroshi ^a   Mizoguchi, Kohji ^a   Shiraishi, Shinji ^a   Murai, Toshiaki ^a   Kato, Shinzi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041125374     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960770c     Document Type: Article

References (31)

1. For reviews on thio- and dithiocarbamates: (a) Organic Compounds of Sulfur, Selenium, and Tellurium; Special Periodical Reports 1-6; The Chemical Society: London, 1970-1981. (b) Coucouvanis, D. Prog. Inorg. Chem. 1979, 26, 301; 1972, 11, 233. (c) The Dithiocarbamates and Related Compounds; Thorn, G. D., Ludwig, R. A., Eds.; Elsevier: New York, 1962.
2. For reviews on thio- and dithiocarbamates: (a) Organic Compounds of Sulfur, Selenium, and Tellurium; Special Periodical Reports 1-6; The Chemical Society: London, 1970-1981. (b) Coucouvanis, D. Prog. Inorg. Chem. 1979, 26, 301; 1972, 11, 233. (c) The Dithiocarbamates and Related Compounds; Thorn, G. D., Ludwig, R. A., Eds.; Elsevier: New York, 1962.
3. For reviews on thio- and dithiocarbamates: (a) Organic Compounds of Sulfur, Selenium, and Tellurium; Special Periodical Reports 1-6; The Chemical Society: London, 1970-1981. (b) Coucouvanis, D. Prog. Inorg. Chem. 1979, 26, 301; 1972, 11, 233. (c) The Dithiocarbamates and Related Compounds; Thorn, G. D., Ludwig, R. A., Eds.; Elsevier: New York, 1962.
4. For reviews on thio- and dithiocarbamates: (a) Organic Compounds of Sulfur, Selenium, and Tellurium; Special Periodical Reports 1-6; The Chemical Society: London, 1970-1981. (b) Coucouvanis, D. Prog. Inorg. Chem. 1979, 26, 301; 1972, 11, 233. (c) The Dithiocarbamates and Related Compounds; Thorn, G. D., Ludwig, R. A., Eds.; Elsevier: New York, 1962.
5. For reviews on selenocarbamates: (a) Sonoda, N. Pure Appl. Chem. 1993, 65, 699. (b) Gysling, H. J. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1986; Vol. 1, p 679.
6. For reviews on selenocarbamates: (a) Sonoda, N. Pure Appl. Chem. 1993, 65, 699. (b) Gysling, H. J. In The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1986; Vol. 1, p 679.
7. For reviews on chalcogenoesters: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 5, p 231. (b) Voss, J. In ref 3a, p 435. (c) Ishii, A.; Nakayama, J. In ref 3a, p 505. (d) Murai, T.; Kato, S. In ref 3a, p 545. (e) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 6, p 461. (f) Reference 2b.
8. For reviews on chalcogenoesters: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 5, p 231. (b) Voss, J. In ref 3a, p 435. (c) Ishii, A.; Nakayama, J. In ref 3a, p 505. (d) Murai, T.; Kato, S. In ref 3a, p 545. (e) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 6, p 461. (f) Reference 2b.
9. For reviews on chalcogenoesters: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 5, p 231. (b) Voss, J. In ref 3a, p 435. (c) Ishii, A.; Nakayama, J. In ref 3a, p 505. (d) Murai, T.; Kato, S. In ref 3a, p 545. (e) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 6, p 461. (f) Reference 2b.
10. For reviews on chalcogenoesters: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 5, p 231. (b) Voss, J. In ref 3a, p 435. (c) Ishii, A.; Nakayama, J. In ref 3a, p 505. (d) Murai, T.; Kato, S. In ref 3a, p 545. (e) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 6, p 461. (f) Reference 2b.
11. For reviews on chalcogenoesters: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 5, p 231. (b) Voss, J. In ref 3a, p 435. (c) Ishii, A.; Nakayama, J. In ref 3a, p 505. (d) Murai, T.; Kato, S. In ref 3a, p 545. (e) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 6, p 461. (f) Reference 2b.
12. For reviews on chalcogenoesters: (a) Ogawa, A.; Sonoda, N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 5, p 231. (b) Voss, J. In ref 3a, p 435. (c) Ishii, A.; Nakayama, J. In ref 3a, p 505. (d) Murai, T.; Kato, S. In ref 3a, p 545. (e) Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 6, p 461. (f) Reference 2b.
13. 2NC(Se)OR′: (e) Bulka, E. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; Wiley: New York, 1977; Vol. 2, p 915. (f) Jensen, K. A.; Due, M.; Holm, A.; Wentrup, C. Acta Chem. Scand. 1966, 20, 2091.
14. 2NC(Se)OR′: (e) Bulka, E. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; Wiley: New York, 1977; Vol. 2, p 915. (f) Jensen, K. A.; Due, M.; Holm, A.; Wentrup, C. Acta Chem. Scand. 1966, 20, 2091.
15. 2NC(Se)OR′: (e) Bulka, E. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; Wiley: New York, 1977; Vol. 2, p 915. (f) Jensen, K. A.; Due, M.; Holm, A.; Wentrup, C. Acta Chem. Scand. 1966, 20, 2091.
16. 2NC(Se)OR′: (e) Bulka, E. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; Wiley: New York, 1977; Vol. 2, p 915. (f) Jensen, K. A.; Due, M.; Holm, A.; Wentrup, C. Acta Chem. Scand. 1966, 20, 2091.
17. 2NC(Se)OR′: (e) Bulka, E. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; Wiley: New York, 1977; Vol. 2, p 915. (f) Jensen, K. A.; Due, M.; Holm, A.; Wentrup, C. Acta Chem. Scand. 1966, 20, 2091.
18. 2NC(Se)OR′: (e) Bulka, E. In The Chemistry of Cyanates and Their Thio Derivatives; Patai, S., Ed.; Wiley: New York, 1977; Vol. 2, p 915. (f) Jensen, K. A.; Due, M.; Holm, A.; Wentrup, C. Acta Chem. Scand. 1966, 20, 2091.
19. Ishihara, H.; Yoshimi, M.; Hara, N.; Ando, H.; Kato, S. Bull. Chem. Soc. Jpn. 1990, 63, 835.
20. (a) Murai, T.; Kakami, K.; Itoh, N.; Kanda, T.; Kato, S. Tetrahedron 1996, 52, 2839.
21. (b) Murai, T.; Hayashi, A.; Kanda, T.; Kato, S. Chem. Lett. 1993, 1469.
22. (c) Kato, S.; Komuro, T.; Kanda, T.; Ishihara, H.; Murai, T. J. Am. Chem. Soc. 1993, 115, 3000.
23. 1C(O)Cl with KSeCN was completed within 30 min under the conditions described as a footnote of Table 1.
24. In the case of aryl isoselenocyanates, the reaction with lithium chalcogenolates (RELi; E = S, Se) has been described: (a) Segi, M.; Nakajima, T. J. Synth. Org. Chem. Jpn. 1995, 53, 678. (b) Sakata, K.; Segi, M.; Nakajima, T. 21st Symposium on Heteroatom Chemistry, Toyama, Japan, 1993; Abstracts, p 231.
25. In the case of aryl isoselenocyanates, the reaction with lithium chalcogenolates (RELi; E = S, Se) has been described: (a) Segi, M.; Nakajima, T. J. Synth. Org. Chem. Jpn. 1995, 53, 678. (b) Sakata, K.; Segi, M.; Nakajima, T. 21st Symposium on Heteroatom Chemistry, Toyama, Japan, 1993; Abstracts, p 231.
26. 77Se NMR spectra for selenoamides: (a) Sekiguchi, M.; Ogawa, A.; Fujiwara, S.-I.; Ryu, I.; Kambe, N. Sonoda, N. Chem. Lett. 1990, 2053. (b) Cullen, E. R.; Guziec, F. S., Jr.; Murphy, C. J.; Wong, T. C.; Andersen, K. K. J. Am. Chem. Soc. 1991, 103, 7055.
27. 77Se NMR spectra for selenoamides: (a) Sekiguchi, M.; Ogawa, A.; Fujiwara, S.-I.; Ryu, I.; Kambe, N. Sonoda, N. Chem. Lett. 1990, 2053. (b) Cullen, E. R.; Guziec, F. S., Jr.; Murphy, C. J.; Wong, T. C.; Andersen, K. K. J. Am. Chem. Soc. 1991, 103, 7055.
28. Also, N-acylthiocarbamic acid esters (RC(O)NHC(S)OR′) exist as a thioxo form in solution (characteristic broad signals due to the N-H proton are observed at δ 8.38-8.96): Oba, M.; Nishiyama, K. Synthesis 1994, 624.
29. -1.
30. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: Oxford, U.K., 1980.
31. Stec, W. J.; Lesiak, K.; Sudol, M. Synthesis 1975, 785.