α,β-环氧酮通过α,β-环氧磺酰腙中间体裂解为酮和炔的反应。

反应机理

反应实例

参考文献

1. Eschenmoser, A.; Felix, D.; Ohloff, G. Helv. Chim. Acta 1967, 50, 708. Albert

2. Eschenmoser (Switzerland, 1925) is best known for his work on, among many others,

the monumental total synthesis of Vitamin B12 with R. B. Woodward in 1973. He now

holds appointments at ETH Zürich and Scripps Research Institute, La Jolla.

3. Tanabe, M.; Crowe, D. F.; Dehn, R. L. Tetrahedron Lett. 1967, 3943.

4. Felix, D.; Müller, R. K.; Horn, U.; Joos, R.; Schreiber, J.; Eschenmoser, A. Helv.

Chim. Acta 1972, 55, 1276.

5. Batzold, F. H.; Robinson, C. H. J. Org. Chem. 1976, 41, 313.

6. Covey, D. F.; Parikh, V. D. J. Org. Chem. 1982, 47, 5315.

7. Chinn, L. J.; Lenz, G. R.; Choudary, J. B.; Nutting, E. F.; Papaioannou, S. E.; Metcalf,

L. E.; Yang, P. C.; Federici, C.; Gauthier, M. Eur. J. Med. Chem. 1985, 20, 235.

8. Dai, W.; Katzenellenbogen, J. A. J. Org. Chem. 1993, 58, 1900.

9. Abad, A.; Arno, M.; Agullo, C.; Cuñat, A. C.; Meseguer, B.; Zaragoza, R. J. J. Nat.

Prod. 1993, 56, 2133.

10. Mück-Lichtenfeld, C. J. Org. Chem. 2000, 65, 1366.

编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Eschenmoser-Tanabe fragmentation，page 214-215.