Preparation of 2-iodo-1,3-butadienes from 1-trimethylsilyl-2,3- butadienes and their functionalizations

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 43-46

  Nishiyama, Takashi ^a   Esumi, Tomoyuki ^a   Iwabuchi, Yoshiharu ^a   Irie, Hiroshi ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 2 IODO 1,3 BUTADIENE; IODINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; MOLECULAR INTERACTION;

EID: 0031983768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10413-0     Document Type: Article

References (18)

1. For the chemistry of 1-trimthylsilyl-2,3-butadienes, see: Hatakeyama, S.; Kawamura, M.; Takano, S. J. Am. Chem. Soc. 1994, 116, 4081-4082 and earlier papers.
2. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc. Chem. Commun. 1993, 125-127.
3. 1H NMR spectrum of the reaction mixture showed the existence of the corresponding vic-diiodoallylsilane 2 and 2-iodobuta-1,3-diene 3 in a ratio of 11:1.
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8. 13C NMR, IR, MS).
9. Cf.: Yanagisawa, A.; Noritake, Y.; Nomura, N.; Yamamoto, H. Synlett 1991, 251-253.
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14. Aufdermarsh, Jr. C.A. J. Org. Chem. 1964, 29, 1994-1996. Kondo, K.; Dobashi, S.; Matsumoto, M. Chemistry Lett. 1976, 1077-1080. Nunomoto, S.; Yamashita, Y. J. Org. Chem. 1979, 44, 4788-4791. Shea, K.J.; Pham, P.Q. Tetrahedron Lett. 1983, 24, 1003-1006.
15. Aufdermarsh, Jr. C.A. J. Org. Chem. 1964, 29, 1994-1996. Kondo, K.; Dobashi, S.; Matsumoto, M. Chemistry Lett. 1976, 1077-1080. Nunomoto, S.; Yamashita, Y. J. Org. Chem. 1979, 44, 4788-4791. Shea, K.J.; Pham, P.Q. Tetrahedron Lett. 1983, 24, 1003-1006.
16. Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. Jin, H.; Uenishi, J.; Christ, W.J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644. Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. ibid. 1986, 108, 6048.
17. Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. Jin, H.; Uenishi, J.; Christ, W.J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644. Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. ibid. 1986, 108, 6048.
18. Takai, K.; Kimura, K.; Kuroda, T.; Hiyama, T.; Nozaki, H. Tetrahedron Lett. 1983, 24, 5281. Jin, H.; Uenishi, J.; Christ, W.J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644. Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. ibid. 1986, 108, 6048.