加热条件下1,5-二烯经过3,3-σ重排得到重排的1,5-二烯的反应。

此反应也可以通过钯催化进行。

【Overman LE, J Am Chem Soc, 1982, 104, 7225】

反应机理

3,3-σ重排

反应实例

2-(3-indolyl)-4-pentenonitrile (5). A solution of 4 (0.1 mmol) in PhMe (0.5 mL) was refluxed for 15 min. Evaporation in vacuum and chromatography (silica gel, hexanes–EA, 1:2) of the residue gave 5 (61%).

【Kawasaki T, J Org Chem, 2001, 66, 1200】

相关文献

1 Cope AC J Am Chem Soc 1940 2 441

2 Vogel E Liebigs Ann 1958 615 1

3 Overman LE J Am Chem Soc 1982 104 7225

4 Lutz RP Chem Rev 1984 84 205

5 McDowell DW J Org Chem 1986 51 183

6 Baldwin JE J Org Chem 1987 52 676

7 Blechert S Synthesis 1989 71

8 Schneider C Synlett 2001 1079

9 Kawasaki T J Org Chem 2001 66 1200

10 Gajewski JJ ARKIVOC 2002 ix 18

11 Zaghdoudi R Org Lett 2003 5 3631

12 Banerji M Tet Lett 2004 45 8183

13 Mahajan MP Tetrahedron 2006 62 11267

14 Cruces J Tet Lett 2008 49 2002

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 97.