Oxidative coupling of methyl phenyl sulfide via sulfonium formation using an oxovanadium complex

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1912-1913

  Yamamoto, Kimihisa ^a,b   Kobayashi, Shintaro ^a   Shouji, Eiichi ^a   Tsuchida, Eishun ^a  

^a WASEDA UNIVERSITY   (Japan)

^b PREST ^*

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000922145     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951490u     Document Type: Article

References (15)

1. Riley, D. P.; Smith, M. R.; Correa, P. E. J. Am. Chem Soc. 1988, 110, 177.
2. Roush, D. M.; Price, E. M.; Templeton, L. K.; Templeton, D. H.; Heathcock, C. H. J. Am. Chem. Soc. 1979, 101, 2971. Yamamto, K.; Shouji, E.; Nishide, H.; Tsuchida E. J. Am. Chem. Soc. 1993, 115, 5819. Anderson, K. K.; Caret, R. L.; Karup-Nielsen, I. J. Am. Chem. Soc., 1974, 96, 8020.
3. Roush, D. M.; Price, E. M.; Templeton, L. K.; Templeton, D. H.; Heathcock, C. H. J. Am. Chem. Soc. 1979, 101, 2971. Yamamto, K.; Shouji, E.; Nishide, H.; Tsuchida E. J. Am. Chem. Soc. 1993, 115, 5819. Anderson, K. K.; Caret, R. L.; Karup-Nielsen, I. J. Am. Chem. Soc., 1974, 96, 8020.
4. Roush, D. M.; Price, E. M.; Templeton, L. K.; Templeton, D. H.; Heathcock, C. H. J. Am. Chem. Soc. 1979, 101, 2971. Yamamto, K.; Shouji, E.; Nishide, H.; Tsuchida E. J. Am. Chem. Soc. 1993, 115, 5819. Anderson, K. K.; Caret, R. L.; Karup-Nielsen, I. J. Am. Chem. Soc., 1974, 96, 8020.
5. Yamamoto, K.; Oyaizu, K.; Iwasaki, N.; Tsuchida, E. Chem. Lett. 1993 1223. Tsuchida, E.; Yamamoto, K.; Oyaizu, K.; Iwasaki, N.; Anson, F. C. Inorg. Chem. 1994, 33, 1056.
6. Yamamoto, K.; Oyaizu, K.; Iwasaki, N.; Tsuchida, E. Chem. Lett. 1993 1223. Tsuchida, E.; Yamamoto, K.; Oyaizu, K.; Iwasaki, N.; Anson, F. C. Inorg. Chem. 1994, 33, 1056.
7. 2 (3.2 g, 94%).
8. 2 was added. Tetrachloroethane was carefully added from a burette to the second vessel to keep the pressure at 1 atm. Oxygen consumption was measured from the net amount of the tetrachloroethane added during the reaction.
9. 4: C, 48.48; H, 4 36. Found: C, 48. 40; H, 4.38.
10. 2: C, 67.2; H, 5.21. Found: C, 66.8; H, 5.28.
11. 4.
12. +-(V) and a vanadium(III) species. Yamamoto, K.; Tsuchida, E.; Nishide, H.; Jikei, M.; Oyaizu, K. Macromolecules 1993, 26, 3432.
13. +-(V) and a vanadium(III) species. Yamamoto, K.; Tsuchida, E.; Nishide, H.; Jikei, M.; Oyaizu, K. Macromolecules 1993, 26, 3432.
14. +]. This means that the two-electron transfer is facilitated at the small potential separation.
15. It is presumed that the reaction proceeds via formation of a vanadium-sulfide dication complex through a two-electron transfer. However, the structure of active sulfide species has not yet been identified.