Feldman烯烃环戊烷合成反应

在自由基催化下，烯烃或炔烃和烯基环丙烷反应得到烯基环戊烷或烯基环戊烯的反应。类似反应：Vinylcyclopropane-cyclopentene rearrangement（烯基环丙烷-环戊烯重排）

反应机理

反应实例

Vinylcyclopentenes (3a) and (3b).To vinylcyclopropane 1 (150 mg, 0.68 mmol) and methyl butynoate 2 (1.26 g, 12.9 mmol) in PhH (6 mL) under Ar was added dropwise a deoxygenated solution of Ph2S2 (190 mg, 0.86 mmol) and AIBN (27 mg, 0,17 mmol) in PhH (40 mL) in ca 30 h under sunlamp irradiation. The mixture was kept at r.t. till 1 was consumed (TLC). Evaporation in vacuum

and flash chromatography (silica gel, 5% Et2O in hexane) afforded 96 mg of 3a and 3b in a 1.5:1 ratio (oil, 41%). Chromatography allows isolation of individual stereoisomers.

【Feldman KS, Tet Lett., 1989, 30, 5845】

相关文献

1 Feldman KS J Am Chem Soc 1986 108 1328

2 Feldman KS J Am Chem Soc 1988 110 3300

3 Feldman KS J Am Chem Soc 1989 111 4878

4 Feldman KS Tet Lett 1989 30 5845

5 Feldman KS Tetrahedron 1989 45 2969

6 Feldman KS J Org Chem 1992 57 100

7 Singleton DA Synlett 1994 273

8 Byers JH Synth Comm 2007 37 1865

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 151.