丁二酸酐类化合物在镍催化下加热脱羧生成烯烃的反应。

反应操作

1-Methoxycarbonylbicyclo[2.2.1]hept-2-ene (2). 1 (9.45 g, 0.042 mol) and fresh (Ph3P)2Ni(CO)2 (5.39 g, 0.008 mol) in anhyd diglyme (75 mL) was refluxed for 6 h till 1880 mL of gas (1 equiv each of CO and CO2) had been collected. The solvent was distilled together with 2 at 40 ℃, 2.5 mm. Diglyme (50 mL) was added to the black mixture which was again distilled to dryness at 51 ℃, 0.02 mm. The combined distillates were poured into 800 mL of H2O and extracted four times with 100 mL pentane. The organic layers on work up gave 5.82 g (91%) of 2.

【Grunewald GL, J Org Chem., 1978, 43, 3074】

相关文献

1 Rose JD J Chem Soc 1950 69

2 Trost BM, Chert F Tet Lett 1971 2603

3 Cramer R J Org Chem 1975 40 2267

4 Jennings PW J Org Chem 1975 40 260

5 Flood TC Tet Lett 1977 3861

6 Grunewald GL J Org Chem 1978 43 3074

7 Tsuzi J J Am Chem Soc 1982 104 5844

8 Tsuzi J Tetrahedron 1987 43 4107

9 Matsuura A Jpn Kokai Tokyo 2008 23 958

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 492.