Cloke-Wilson环丙基酮重排反应

环丙基酮或环丙基亚胺在Lewis酸催化下重排为二氢呋喃或二氢吡咯的反应。加热或光照条件下也可引发此反应。

反应机理

反应操作

2-Methyl-3-phenyl-1-pyrroline (5).To stirred imine 3 (4.15 g) in 10 mL dry ether was added gradually 30 mL of a sat ethereal solution of HCl under N2 to give a precipitate. The ether was evaporated at 60 C. The residue was rapidly heated to 140 C and stirred for 10 min. The product (yellow) was leached with dil HCl and washed well with ether. Basification of the aq layer and ether extraction

afforded 2.32 g (56%) of 5, bp 58–60 C.

相关文献

1 Cloke JB J Am Chem Soc 1929 51 1174

2 Wilson CL J Am Chem Soc 1947 69 3002

3 Stevens RV J Am Chem Soc 1968 90 5576

4 Alonso ME J Org Chem 1980 45 4532

5 Hudlicky T Org React 1986 33 247

6 Sampedro D J Org Chem 2005 70 6976

7 Shi M J Org Chem 2005 70 8645

8 Ma S Pure Appl Chem 2008 80 695

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 92.