咨询电话:021-58952328
Arndt–Eistert同系化反应2019-02-25


羧酸经过重氮甲烷处理得到多一个碳的同系物的反应。

反应机理


反应实例




参考文献

  1. Arndt, F.; Eistert, B. Ber. 1935, 68, 200-208. Fritz Arndt (1885-1969) was born in Hamburg, Germany. He discovered the Arndt-Eistert homologation at the University of Breslau where he extensively investigated the synthesis of diazomethane and its reactions with aldehydes, ketones, and acid chlorides. Fritz Arndt’s chain-smoking of cigars ensured that his presence in the laboratories was always well advertised. Bernd Eistert (1902-1978), born in Ohlau, Silesia, was Arndt’s Ph.D. student. Eistert later joined I. G. Farbenindustrie, which became BASF after the Allies broke up the conglomerate following WWII.

Fritz Arndt (1885-1969) 出生于德国汉堡。他在布雷斯劳大学任教期间发现了Arndt-Eister同系化反应,在这期间他主要研究重氮甲烷的合成以及重氮甲烷和醛酮及酰氯的反应。 另外有趣的是Fritz Arndt广为人知的形象是一个做实验的老烟鬼。Bernd Eistert (1902-1978), 出生于Ohlau, Silesia,是Arndt的 Ph.D.学生。他后来进入了法本化学工业股份公司(二战同盟国胜利后被重组为巴斯夫)工作。

2. Podlech, J.; Seebach, D. Angew. Chem. Int. Ed. 1995, 34, 471-472.

3. Matthews, J. L.; Braun, C.; Guibourdenche, C.; Overhand, M.; Seebach, D. In

Enantioselective Synthesis of -Amino Acids Juaristi, E. ed.; Wiley-VCH: Weinheim,

Germany, 1996, pp 105126. (Review).

4. Katritzky, A. R.; Zhang, S.; Fang, Y. Org. Lett. 2000, 2, 37893791.

5. Vasanthakumar, G.-R.; Babu, V. V. S. Synth. Commun. 2002, 32, 651657.

6. Chakravarty, P. K.; Shih, T. L.; Colletti, S. L.; Ayer, M. B.; Snedden, C.; Kuo, H.;

Tyagarajan, S.; Gregory, L.; Zakson-Aiken, M.; Shoop, W. L.; Schmatz, D. M.;

Wyvratt, M. J.; Fisher, M. H.; Meinke, P. T. Bioorg. Med. Chem. Lett. 2003, 13,

147150.

7. Gaucher, A.; Dutot, L.; Barbeau, O.; Hamchaoui, W.; Wakselman, M.; Mazaleyrat, J.-

P. Tetrahedron: Asymmetry 2005, 16, 857864.

8. Podlech, J. In Enantioselective Synthesis of -Amino Acids (2nd Edn.) Wiley: Hoboken,

NJ, 2005, pp 93106. (Review).

9. Spengler, J.; Ruiz-Rodriguez, J.; Burger, K.; Albericio, F. Tetrahedron Lett. 2006, 47,

45574560.

10. Toyooka, N.; Kobayashi, S.; Zhou, D.; Tsuneki, H.; Wada, T.; Sakai, H.; Nemoto, H.;

Sasaoka, T.; Garraffo, H. M.; Spande, T. F.; Daly, J. W. Bioorg. Med. Chem. Lett.

2007, 17, 58725875.

11. Fuchter, M. J. Arndt–Eistert Homologation. In Name Reactions for Homologations-

Part I; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 336349. (Review).

12. Saavedra, C. J.; Boto, A.; Hernández, R. Org. Lett. 2012, 14, 35423545.

编译自:J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications,  Arndt–Eistert homologation,page10-11.

最新产品
园区介绍