Preparation of alkenyl sulfides by the olefination of thiolesters using thioacetals

Chemistry Letters

Volumn , Issue 2, 1998, Pages 115-116

  Takeda, Takeshi ^a   Watanabe, Mikako ^a   Nozaki, Naoki ^a   Fujiwara, Tooru ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032373380     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.115     Document Type: Article

References (9)

1. For examples; B. M. Trost and A. C. Lavoie, J. Am. Chem. Soc., 105, 5075 (1983), and references cited therein; T. Takeda, H. Furukawa, M. Fujimori, K. Suzuki, and T. Fujiwara, Bull. Chem. Soc. Jpn., 57, 1863 (1984); H. Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, and N. Sonoda, J. Am. Chem. Soc., 114, 5902 (1992); T. Ishiyama, K. Nishijima, N. Miyaura, and A. Suzuki, J. Am. Chem. Soc., 115, 7219 (1993).
2. For examples; B. M. Trost and A. C. Lavoie, J. Am. Chem. Soc., 105, 5075 (1983), and references cited therein; T. Takeda, H. Furukawa, M. Fujimori, K. Suzuki, and T. Fujiwara, Bull. Chem. Soc. Jpn., 57, 1863 (1984); H. Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, and N. Sonoda, J. Am. Chem. Soc., 114, 5902 (1992); T. Ishiyama, K. Nishijima, N. Miyaura, and A. Suzuki, J. Am. Chem. Soc., 115, 7219 (1993).
3. For examples; B. M. Trost and A. C. Lavoie, J. Am. Chem. Soc., 105, 5075 (1983), and references cited therein; T. Takeda, H. Furukawa, M. Fujimori, K. Suzuki, and T. Fujiwara, Bull. Chem. Soc. Jpn., 57, 1863 (1984); H. Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, and N. Sonoda, J. Am. Chem. Soc., 114, 5902 (1992); T. Ishiyama, K. Nishijima, N. Miyaura, and A. Suzuki, J. Am. Chem. Soc., 115, 7219 (1993).
4. For examples; B. M. Trost and A. C. Lavoie, J. Am. Chem. Soc., 105, 5075 (1983), and references cited therein; T. Takeda, H. Furukawa, M. Fujimori, K. Suzuki, and T. Fujiwara, Bull. Chem. Soc. Jpn., 57, 1863 (1984); H. Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, and N. Sonoda, J. Am. Chem. Soc., 114, 5902 (1992); T. Ishiyama, K. Nishijima, N. Miyaura, and A. Suzuki, J. Am. Chem. Soc., 115, 7219 (1993).
5. Y. Horikawa, M. Watanabe, T. Fujiwara, and T. Takeda, J. Am. Chem. Soc., 119, 1127 (1997).
6. 3) of vinyl protons of alkenyl sulfides 4 and sulfones 5 are as follows: 4a (E; 5.34, Z; 5.64); 5a (E; 6.70, Z; 6.13); 4b (E; 5.40, Z; 5.58); 5b (E; 6.71, Z; 6.01); 4c (E; 5.59, Z; 5.64); 5c (E; 6.69, Z; 6.03); 4d (E; 5.85, Z; 5.89); 5d (E; 6.91, Z; 6.00); 4e (Z; 6.00); 5e (Z; 6.33); 4f (E; 5.44, Z; 5.60); 5f (E; 6.75, Z; 6.04); 4g (E; 5.62, Z; 5.65); 5g (E; 6.72, Z; 6.07); 4h (E; 5.64, Z; 5.51); 5h (E; 6.67, Z; 5.73); 4i (E; 6.30, Z; 6.55); 5i (E; 7.59, Z; 7.13); 4j (E; 6.48, Z; 6.59); 5j (E; 7.56, Z; 7.12). The similar spectroscopic data of a series of 1-arylalkenyl phenyl sulfides were obtained; T. Takeda, F. Kanamori, M. Masuda, and T. Fujiwara, Tetrahedron Lett., 32, 5567 (1991).
7. K. Takai, O. Fujimura, Y. Kataoka, and K. Utimoto, Tetrahedron Lett., 30, 211 (1989).
8. Y. Horikawa, T. Nomura, M. Watanabe, T. Fujiwara, and T. Takeda, J. Org. Chem., 62, 3678 (1997); T. Takeda, H. Shimokawa, Y. Miyachi, and T. Fujiwara, J. Chem. Soc., Chem. Commun., 1997, 1055.
9. Y. Horikawa, T. Nomura, M. Watanabe, T. Fujiwara, and T. Takeda, J. Org. Chem., 62, 3678 (1997); T. Takeda, H. Shimokawa, Y. Miyachi, and T. Fujiwara, J. Chem. Soc., Chem. Commun., 1997, 1055.