Models for the homogeneous hydrodesulfurization of benzothiophene: Sequential insertion of manganese into the C(aryl)-S and C(vinyl)-S bonds, followed by metallathiacycle ring contraction

Organometallics

Volumn 16, Issue 26, 1997, Pages 5604-5606

  Dullaghan, Conor A ^a   Zhang, Xiao ^a   Walther, Dane ^a   Carpenter, Gene B ^a   Sweigart, Dwight A ^a   Meng, Qingjin ^b  

^a BROWN UNIVERSITY   (United States)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000895253     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970728x     Document Type: Article

References (32)

1. (a) Sanchez-Delgado, R. A. J. Mol. Catal. 1994, 86, 287.
2. (b) Angelici, R. J. Bull. Soc. Chim. Belg. 1995, 104, 265.
3. (c) Startev, A. N. Catal. Rev.-Sci. Eng. 1995, 37, 353.
4. (d) Bianchini, C.; Meli, A. J. Chem. Soc., Dalton Trans. 1996, 801.
5. (a) Willey, C.; Iwao, M.; Castle, R. N.; Lee, M. L. Anal. Chem. 1981, 53, 400.
6. (b) Kabe, T.; Ishihara, A.; Tajima, H. Ind. Eng. Chem. Res. 1992, 31, 1577.
7. (a) Dong, L.; Duckett, S. B.; Ohman, K. F.; Jones, W. D. J. Am. Chem. Soc. 1992, 114, 151.
8. (b) Choi, M.-G.; Angelici, R. J. Organometallics 1992, 11, 3328.
9. (c) Bianchini, C.; Herrera, V.; Jimenez, M. V.; Meli, A.; Sanchez-Delgado, R.; Vizza, F. J. Am. Chem. Soc. 1995, 117, 8567.
10. (d) Garcia, J. J.; Mann, B. E.; Adams, H.; Bailey, N. A.; Maitlis, P. M. J. Am. Chem. Soc. 1995, 117, 2179.
11. (a) Ogilvy, A. E.; Draganjac, M.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1988, 7, 1171.
12. (b) Jones, W. D.; Dong, L. J. Am. Chem. Soc. 1991, 113, 559.
13. (c) Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Moneti, S.; Herrera, V.; Sanchez-Delgado, R. A. J. Am. Chem. Soc. 1994, 116, 4370.
14. (d) Bianchini, C.; Herrera, V.; Jimenez, M. V.; Laschi, F.; Meli, A.; Sanchez-Delgado, R.; Vizza, F.; Zanello, P. Organometallics 1995, 14, 4390.
15. (e) Bianchini, C.; Meli, A.; Patinec, V.; Sernau, V.; Vizza, F. J. Am. Chem. Soc. 1997, 119, 4945.
16. Myers, A. W.; Jones, W. D.; McClements, S. M. J. Am. Chem. Soc. 1995, 117, 1704.
17. Dullaghan, C. A.; Sun, S.; Carpenter, G. B.; Weldon, B.; Sweigart, D. A. Angew. Chem. 1996, 108, 234; Angew. Chem., Int. Ed. Engl. 1996, 35, 212.
18. Dullaghan, C. A.; Sun, S.; Carpenter, G. B.; Weldon, B.; Sweigart, D. A. Angew. Chem. 1996, 108, 234; Angew. Chem., Int. Ed. Engl. 1996, 35, 212.
19. Sun, S.; Dullaghan, C. A.; Sweigart, D. A. J. Chem. Soc., Dalton Trans. 1996, 4493.
20. (a) Chen, J.; Daniels, L. M.; Angelici, R. J. J. Am. Chem. Soc. 1991, 113, 2544.
21. (b) Dailey, K. M. K.; Rauchfuss, T. B.; Rheingold, A. L.; Yap, G. P. A. J. Am. Chem. Soc. 1995, 117, 6396.
22. (c) Bianchini, C.; Jimenez, M. V.; Mealli, C.; Meli, A.; Moneti, S.; Patinec, V.; Vizza, F. Angew. Chem. 1996, 108, 1845; Angew. Chem., Int. Ed. Engl. 1996, 35, 1706.
23. (c) Bianchini, C.; Jimenez, M. V.; Mealli, C.; Meli, A.; Moneti, S.; Patinec, V.; Vizza, F. Angew. Chem. 1996, 108, 1845; Angew. Chem., Int. Ed. Engl. 1996, 35, 1706.
24. (a) Jackson, J. D.; Villa, S. J.; Bacon, D. S.; Pike, R. D. Organometallics 1994, 13, 3972.
25. (b) Sun, S.; Yeung, L. K.; Sweigart, D. A.; Lee, T.-Y.; Lee, S. S.; Chung, Y. K.; Switzer, S. R.; Pike, R. D. Organometallics 1995, 14, 2613.
26. 2), 1.56 (t, J = 7.5 Hz, Me). Anal. Calcd: C, 40.21; H 2.60. Found: C, 40.48; H 2.45.
27. Loozen, G. J. Org. Chem. 1974, 38, 1036.
28. 2), 1.36 (t, J = 7.6, Me).
29. 2), 1.35 (t, J = 7.6 Hz, Me).
30. 2), 1.36 (t, J = 6.4 Hz, Me).
31. -1, θ range 1.69-26.33°, 236 variables refined with 3509 independent reflections to final R indices (I > 2σ(I)) of R = 0.0467 and wR2 = 0.1043, and GOF = 0.980.
32. Camiletti, C.; Dullaghan, C. A.; Zhang, X.; Meng, Q.; Carpenter, G. B.; Sweigart, D. A. Unpublished results.