Three syntheses of trans-cyclooctane-1,2-dithiol by ring opening of cis-cyclooctene episulfoxide with ammonium thiocyanate followed by reduction and reductions of trans-1,2-di(thiocyanato)cyclooctane and trans-1,2-cyclooctyl trithiocarbonate

Journal of Sulfur Chemistry

Volumn 30, Issue 3-4, 2009, Pages 236-244

  Ishii, Akihiko ^a   Ono, Aya ^a   Nakata, Norio ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

1,2 dithiol; Episulfoxide; Reduction; Ring opening; Thiocyanation; Trithiocarbonate

Indexed keywords

ALUMINUM COMPOUNDS; ETHERS; NITROGEN COMPOUNDS;

% REDUCTIONS; 1,2-DITHIOL; CIS-CYCLOOCTENE; CYCLOOCTANES; DIISOBUTYLALUMINUM HYDRIDE; DITHIOLS; EPISULPHOXIDE; RING OPENING; THIOCYANATION; TRITHIOCARBONATE;

LITHIUM COMPOUNDS;

EID: 71149085757     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990902839435     Document Type: Article

References (48)

1. (a) Beckerle, K.; Manivannan, R.; Lian, B.; Meppelder, G.-J. M.; Raabe, G.; Spaniol, T.P.; Ebeling, H.; Pelascini, F.; Mülhaupt, R.; Okuda, J. Angew. Chem. Int. Ed. 2007, 46, 4790-4793
2. (b) Meppelder, G.-J.M.; Beckerle, K.; Manivannan, R.; Lian, B.; Raabe, G.; Spaniol, T.P.; Okuda, J. Chem. Asian J. 2008, 3, 1312-1323
3. (c) Marcseková, K.; Loos, C.; Rominger, F.; Doye, S. Synlett. 2007, 2564-2568.
4. Cohen, A.; Yeori, A.; Goldberg, I.; Kol, M. Inorg. Chem. 2007, 46, 8114-8116.
5. (a) Carpentier, J.-F. Angew. Chem. Int. Ed. 2007, 46, 6404-6406
6. (b) Konkol, M.; Kondracka, M.; Voth, P.; Spaniol, T.P.; Okuda, J. Organometallics 2008, 27, 3774-3784
7. (c) Gall, B.T.; Pelascini, F.; Ebeling, H.; Beckerle, K.; Okuda, J.; Mülhaupt, R. Macromolecules 2008, 41, 1627-1633
8. (d) Capacchione, C.; Avagliano, A.; Proto, A. Macromolecule 2008, 41, 4573-4575
9. (e) Lian, B.; Beckerle, K.; Spaniol, T.P.; Okuda, J. Angew. Chem. Int. Ed. 2007, 46, 8507-8510
10. (f) Capacchione, C.; Manivannan, R.; Barone, M.; Beckerle, K.; Centore, R.; Oliva, L.; Proto, A.; Tuzi, A.; Spaniol, T.P.; Okuda, J. Organometallics 2005, 24, 2971-2982
11. (g) Capacchione, C.; Proto, A.; Ebeling, H.; Mühaupt, R.; Möller, K.; Spaniol, T.P.; Okuda, J. J. Am. Chem. Soc. 2003, 125, 4964-4965.
12. (a) Sellmann, D.; Lauderbach, F.; Heinemann, F.W. Eur. J. Inorg. Chem. 2005, 371-377
13. (b) Sellmann, D.; Blum, D.C.F.; Heinemass, F.W.; Sutter, J. Eur. J. Inorg. Chem. 2003, 418-426
14. (c) Sellmann, D.; Gottschalk-Gaudig, T.; Heinemann, F.W. Inorg. Chem. 1998, 37, 3982-3988.
15. (d) Sellmann, D.; Gottschalk-Gaudig, T.; Heinemann, F.W.; Knoch, F. Chem. Ber./Recueil 1997, 130, 571-579
16. (e) Sellmann, D.; Käppler, J.; Moll, M. J. Am. Chem. Soc. 1993, 115, 1830-1835.
17. Bosnich, B.; Phillip, A.T. J. Chem. Soc. 22 (A) 1970, 264-271.
18. Kim, Y.-S.; Tian, W.; Kim, Y.; Jun, M.J. Polyhedron 1997, 16, 3807-3814.
19. Amendola, V.; Mangano, C.; Pallavicini, P.; Zema, M. Inorg. Chem. 2003, 42, 6056-6062.
20. Knight, P.D.; Scott, P. Coord. Chem. Rev. 2003, 242, 125-143.
21. Ishii, A.; Suzuki, M.; Yamashita, R. Tetrahedron 2006, 62, 5441-5447.
22. Ishii, A.; Suzuki, M.; Nakata, N. Phosphorus Sulfur Silicon Relat. Elem. 2009, 184, 1184-1205.
23. (a) Inoue, S.; Tezuka, T.; Oae, S. Phosphorus Sulfur 1978, 4, 219-221
24. (b) Bartlett, P.D.; Ghosh, T. J. Org. Chem. 1987, 52, 4937-4943
25. (c) Kustos, M.; Steudel, R. J. Org. Chem. 1995, 60, 8056-8061
26. (d) Shields, T.C.; Kurtz, A.N. J. Am. Chem. Soc. 1969, 91, 5415-5416.
27. (a) Iqbal, S.M.; Owen, L.N. J. Chem. Soc. 1960, 1030-1036
28. (b) Kardouche, N.G.; Owen, L.N. J. Chem. Soc. Perkin I 1975, 754-761
29. (c) Ali, M.E.; Kardouche, N.G.; Owen, L.N. J. Chem. Soc. Perkin I 1975, 748-754
30. (d) Culvenor, C.C.J.; Davies, W.; Pausacker, K.H. J. Chem. Soc. 1946, 1050-1052.
31. (a) Lalancette, J.M.; Laliberté, M. Tetrahedron Lett. 1973, 1401-1404
32. (b) Bernardo, M.M.; Brown, S.; Li, Z.-H.; Fridman, R.; Mobashery, S. J. Biol. Chem. 2002, 277, 11201-11207
33. (c) Sato, R.; Okanuma, M.; Chiba, S.; Ogawa, S. Tetrahedron Lett. 1994, 35, 891-894
34. (d) Kondo, M.; Horikoshi, H.; Takeuchi, M. Jpn. Kokai Tokkyo Koho 2004, JP2004107278A2 (Chem. Abstr. 140:303309)
35. (e) Iranpoor, N.; Firouzabadi, H.; Chitsazi, M.; Jafari, A.A. Tetrahedron 2002, 58, 7037-7042.
36. (a) Block, E.; Yencha, A.J.; Aslam, M.; Eswarakrishnan, V.; Luo, J.; Sano, A. J.Am. Chem. Soc. 1988, 110, 4748-4753
37. (b) Okazaki, R.; O-oka, M.; Akiyama, T.; Inamoto, N.; Niwa, J.; Kato, S. J. Am. Chem. Soc. 1987, 109, 5413-5419.
38. (a) (a)Vilsmaier, E.; Becker, G. Synthesis 1975, 55-57
39. (b) Harmon, J.P.; Field, L. J. Org. Chem. 1986, 51, 5235-5240.
40. (a) Kondo, K.; Negishi, A.; Ojima, I. J. Am. Chem. Soc. 1972, 94, 5786-5793
41. (b) Akasaka, T.; Kako, M.; Sonobe, H.; Ando, W. J. Am. Chem. Soc. 1988, 110, 494-496
42. (c) Manser, G.E.; Mesure, A.D.; Tillett, J.G. Tetrahedron Lett. 1968, 3153-3156
43. (d) Hartzell, G.E.; Paige, J.N. J. Am. Chem. Soc. 1966, 88, 2616-2617.
44. Corey, E.J.; Carey, F.A.; Winter, R.A.E. J. Am. Chem. Soc. 1965, 87, 934-935.
45. Fringuelli, F.; Germani, R.; Pizzo, F.; Savelli, G. Tetrahedron Lett. 1989, 30, 1427-1428.
46. Iranpoor, N.; Kazemi, F. Synthesis 1996, 821-822.
47. Pettitt, D.J.; Helmkamp, G.K. J. Org. Chem. 1964, 29, 2702-2706.
48. Nakayama, J.; Tajima, Y.; Xue-hua, P.; Sugihara, Y. J. Am. Chem. Soc. 2007, 129, 7250.