Migita-Sano邻苯醌二甲烷合成

酸催化下，邻(1-羟基烷基)苄基三丁基锡烷通过1,4-消除得到邻苯醌二甲烷的反应。邻苯醌二甲烷不稳定，可以通过亲二烯体进行Diels–Alder反应捕获得到加成产物。

反应机理

反应实例

Anhydride (5).To 2 (100 mg, 0.24 mmol) and 4 (71.6 mg, 0.73 mmol) in DCM (0.2 mL) was added TFA (0.038 mL, 0.48 mmol) at 20 C and the mixture was stirred for 1 h. DCM, TFA and unreacted 4 were removed in vacuo and the residue was treated with n-heptane (1 mL) to afford 47 mg of 5 (96%).

【Migita T, Sano H, J Am Chem Soc, 1988, 110, 2014】

相关文献

1 Kauffmann T Angew Chem Int 1982 21 410

2 Migita T, Sano H J Am Chem Soc 1988 110 2014

3 Kuwano R Chem Lett 2005 34 728

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 319-320.