University Chemistry ›› 2025, Vol. 40 ›› Issue (12): 187-191.doi: 10.12461/PKU.DXHX202510104
• Between Teacher and Student • Previous Articles Next Articles
Hongyu Cheng1, Ruiyao Wang2, Xingwen Sun1
Received:2025-10-29
Accepted:2025-12-03
Published:2025-12-27
Contact:
Xingwen Sun
E-mail:sunxingwen@fudan.edu.cn
Hongyu Cheng, Ruiyao Wang, Xingwen Sun. Mechanistic Study of the Classic Hofmann Elimination Reaction[J].University Chemistry, 2025, 40(12): 187-191.
| [1] Saytzeff, A. J. Liebigs Ann. Chem. 1875, 179, 296. [2] (a) von Hofmann, A. W. Ber. 1881, 14, 659. (b) von Hofmann, A. W. Ber. 1881, 14, 494. [3] (a) von Hofmann, A. W. Phil. Trans. R. Soc. 1851, 141, 357. (b) von Hofmann, A. W. J. Liebigs Ann. Chem. 1851, 78, 253. [4] (a) Booth, H.; Bostock, A. H.; Franklin, N. C.; Griffiths, D. V.; Little, J. H. J. C. S. Perkin I 1978, 899. (b) Cope, A. C.; Trumbull, E. R. Organic Reactions, Vol. XI.; John Wiley & Sons, Inc.: New York, NY, USA, 1960. (c) Doering, W. von E.; Meislich, H. J. Am. Chem. Soc. 1952, 74, 2099. [5] Shiner Jr., V. J.; Smith, M. L. J. Am. Chem. Soc. 1958, 80, 4095. [6] Coke, J. L.; Cooke, M. P. J. Am. Chem. Soc. 1967, 89, 6701. [7] Cope, A. C.; LeBel, N. A.; Moore, P. T.; Moore, W. R. J. Am. Chem. Soc. 1961, 83, 3861. [8] (a)叶秀林. 大学化学, 1993, 8 (3), 12. (b)郭静, 鹿笃仁, 叶秀林. 高等学校化学学报, 1985, No. 6, 1000. (c)徐筱杰, 姚振贵, 叶秀林, 唐有祺, 傅亨, 钱民协. 物理化学学报, 1989, 5, 398. (d)马殿英, 牛梅菊, 崔庆新, 葛树丰, 穆依群, 叶秀林. 北京大学学报(自然科学版), 1990, No. 26, 214. [9] (a) Wade Jr., L. G. Organic Chemistry, 5th ed.; Pearson Education Inc.: Upper Saddle River, NJ, USA, 2003. (b) McMurry, J. Organic Chemistry: A Tenth Edition; OpenStax: Houston, TX, USA, 2023. [10] 邢其毅, 裴伟伟, 徐瑞秋, 裴坚. 基础有机化学(上册). 第4版. 北京: 北京大学出版社, 2016. [11] Booth, H.; Franklin, N. C.; Gidley, G. C. J. Chem. Soc. C 1968, 1891. [12] Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 16, Revision A. 03; Gaussian Inc.: Wallingford, CT, USA, 2016. [13] Becke, A. D. J. Chem. Phys. 1993, 98, 5648. [14] Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104. [15] Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456. [16] (a) Fukui, K. Acc. Chem. Res. 1981, 14, 363. (b) Hratchian, H. P.; Schlegel, H. B. Finding Minima, Transition States, and Reaction Pathways on Potential Energy Surfaces. In Theory and Applications of Computational Chemistry: The First 40 Years; Dykstra, C. E., Frenking, G., Kim, K. S., Scuseria, G. Eds.; Elsevier: Amsterdam, The Netherlands, 2005; pp. 195-249. [17] Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378. [18] Ho, J.; Klamt, A.; Coote, M. L. J. Phys. Chem. A 2010, 114, 13442. [19] Legault, C. Y. CYLview20. [2025-12-03]. http://www.cylview.org |
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