Reaction of 1,3-dihalopropene with trialkylmanganate

Chemistry Letters

Volumn , Issue 1, 1998, Pages 73-74

  Kakiya, Hirotada ^a   Inoue, Rie ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032375418     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.73     Document Type: Article

References (13)

1. R. Inoue, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 37, 5377 (1996).
2. H. Kakiya, R. Inoue, H. Shinokubo, and K. Oshima, Tetrahedron Lett., 38, 3275 (1997).
3. Preparation of organozinc species by similar alkyl migration using trialkylzincate was reported. T. Harada, T. Katsuhira, A. Osada, K. Iwazaki, K. Maejima, A. Oku, J. Am. Chem. Soc., 118, 11377 (1996).
4. 1,3-Dibromopropene and 1,3-dichloropropene were purchased from Aldrich Chemical Company, Inc. and Tokyo Kasei Co. Ltd., respectively, and used without further purification. A mixture of 1,3-dichloro-1-butene and 1,1-dichloro-2-butene was prepared according to the reported procedure: L. J. Andrews, J. Am. Chem. Soc., 68, 2584 (1946).
5. 2) in the mixture.
6. 2, 60%) by an addition of benzaldehyde.
7. Preparative methods for allylmanganate have been reported: K. Takai, T. Ueda, T. Hayashi, and T. Moriwake, Tetrahedron Lett., 37, 7049 (1996); T. Hiyama, M. Obayashi, and A. Nakamura, Organometallics, 1, 1249 (1982); T. Hiyama, M. Sawahata, M. Obayashi, Chem. Lett., 1983, 1237; G. Cahiez and P.-Y. Chavant, Tetrahedron Lett., 30, 7373 (1989).
8. Preparative methods for allylmanganate have been reported: K. Takai, T. Ueda, T. Hayashi, and T. Mon wake, Tetrahedron Lett., 37, 7049 (1996); T. Hiyama, M. Obayashi, and A. Nakamura, Organometallics, 1, 1249 (1982); T. Hiyama, M. Sawahata, M. Obayashi, Chem. Lett., 1983, 1237; G. Cahiez and P.-Y. Chavant, Tetrahedron Lett., 30, 7373 (1989).
9. Preparative methods for allylmanganate have been reported: K. Takai, T. Ueda, T. Hayashi, and T. Mon wake, Tetrahedron Lett., 37, 7049 (1996); T. Hiyama, M. Obayashi, and A. Nakamura, Organometallics, 1, 1249 (1982); T. Hiyama, M. Sawahata, M. Obayashi, Chem. Lett., 1983, 1237; G. Cahiez and P.-Y. Chavant, Tetrahedron Lett., 30, 7373 (1989).
10. Preparative methods for allylmanganate have been reported: K. Takai, T. Ueda, T. Hayashi, and T. Mon wake, Tetrahedron Lett., 37, 7049 (1996); T. Hiyama, M. Obayashi, and A. Nakamura, Organometallics, 1, 1249 (1982); T. Hiyama, M. Sawahata, M. Obayashi, Chem. Lett., 1983, 1237; G. Cahiez and P.-Y. Chavant, Tetrahedron Lett., 30, 7373 (1989).
11. 2Mn. We can not deny this possibility and need further study to decide the reaction mechanism.
12. 3MnMtl. Formula Presented
13. 2 gave a complex mixture which mainly contains 1-bromo-1-undecene and 3-bromo-1-undecene.