Citation: Bolin Sun, Jie Chen, Ling Zhou. 乙烯型卤代烃的亲核取代反应[J]. University Chemistry, ;2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032 shu

乙烯型卤代烃的亲核取代反应

College of Chemistry and Materials Science, Northwest University, Xi'an 710127, China

Corresponding author: Ling Zhou, zhoul@nwu.edu.cn
Received Date: 9 October 2024
Revised Date: 6 January 2025

在基础有机化学教材中，乙烯型卤代烃的亲核取代反应通常被认为是难以发生的。然而，随着近年来研究的深入，化学家们发现多例乙烯型卤代烃的亲核取代反应，并将这类反应命名为烯基亲核取代(Nucleophilic vinylic substitution，S_NV)反应。本文主要介绍已提出的S_NV反应的可能机理，并展示几个典型的S_NV反应实例。将这些前沿进展融入课堂教学，不仅有助于学生了解S_NV反应，而且能够丰富现有的亲核取代反应知识体系。
- Vinylic halides,
- S_NV reaction,
- Nucleophilic substitution,
- Reaction mechanism
1. [1]
  Katritzky, A. R.; Brycki, B. E. Chem. Soc. Rev. 1990, 19, 83.
2. [2]
  Hughes, E. D.; Juliusburger, F.; Masterman, S.; Topley, B.; Weiss, J. J. Chem. Soc. 1935, 1525.
3. [3]
  Cowdrey, W. A.; Hughes, E. D.; Ingold, C. K.; Masterman, S.; Scott, A. D. J. Chem. Soc. 1937, 1252.
4. [4]
  Rappoport, Z. Adv. Phys. Org. Chem. 1969, 7, 1.
5. [5]
  Apeloig, Y.; Rappoport, Z. J. Am. Chem. Soc. 1979, 101, 5095.
6. [6]
  Rappoport, Z. Acc. Chem. Res. 1981, 14, 7.
7. [7]
  Modena, G. Acc. Chem. Res. 1971, 4, 73.
8. [8]
  Okuyama, T.; Lodder, G. Adv. Phys. Org. Chem. 2002, 37, 1.
9. [9]
  Rapport, Z. Acc. Chem. Res. 1992, 25, 474.
10. [10]
  Glukhovtsev, M. N.; Pross, A.; Radom, L. J. Am. Chem. Soc. 1994, 116, 5961.
11. [11]
  Kim, C. K.; Hyun, K. H.; Kim, C. K.; Lee, I. J. Am. Chem. Soc. 2000, 122, 2294.
12. [12]
  Fernández, I.; Bickelhaupt, F. M.; Uggerud, E. J. Org. Chem. 2013, 78, 8574.
13. [13]
  Ochiai, M.; Oshima, K.; Masaki, Y. J. Am. Chem. Soc. 1991, 113, 7059.
14. [14]
  Okuyama, T.; Takino, T.; Sato, K.; Ochiai, M. J. Am. Chem. Soc. 1998, 120, 2275.
15. [15]
  Bottini, A. T.; Olsen, R. E. J. Am. Chem. Soc. 1962, 84, 195.
16. [16]
  Shiers, J. J.; Shipman, M.; Hayes, J. F.; Slawin, A. M. Z. J. Am. Chem. Soc. 2004, 126, 6868.
17. [17]
  Miyauchi, H.; Chiba, S.; Fukamizu, J.; Ando, K.; Narasaka, K. Tetrahedron 2007, 63, 5940.
18. [18]
  Lei, M.-Y.; Fukamizu, K.; Xiao, Y.-J.; Liu, W.-M.; Twiddy, S.; Chiba, S.; Ando, K.; Narasaka, K. Tetrahedron Lett. 2008, 49, 4125.
19. [19]
  Chen, M.; Knox, C. D.; Madhusudhanan, M. C.; Tugwell, T. H.; Liu, C.; Liu, P.; Dong, G. B. Nature 2024, 631, 328.
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