Ciamician–Dennsted重排

吡咯和氯仿在氢氧化钠存在下反应制备3-氯吡啶的反应。

反应机理

氢氧化钠和氯仿反应生成二氯卡宾，然后对吡咯进行环丙烷化，重排得到3-氯吡啶。

反应实例

参考文献

1. Ciamician, G. L.; Dennsted, M. Ber. 1881, 14, 1153. Giacomo Luigi Ciamician (1857-1922) was born in Trieste, Italy. Ciamician is considered the father of modern organic photochemistry. Giacomo Luigi Ciamician (1857-1922) 生于意大利

里雅斯特，他被认为是现代有机光化学之父。

2. Wynberg, H. Chem. Rev. 1960, 60, 169-184. (Review).

3. Wynberg, H. and Meijer, E. W. Org. React. 1982, 28, 1-36. (Review).

4. Parham, W. E.; Davenport, R. W.; Biasotti, J. B. J. Org. Chem. 1970, 35, 3775-3779.

5. Král, V.; Gale, P. A.; Anzenbacher, P. Jr.; K. Jursíková; Lynch, V.; Sessler, J. L.

Chem. Comm. 1998, 9-10.

6. Pflum, D. A. Ciamician–Dennsted Rearrangement. In Name Reactions in Heterocyclic Chemistry; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 350354. (Review).

编译自：J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications,  Ciamician–Dennsted rearrangement，page 135.