威斯特法伦-莱特雷重排反应
威斯特法伦-莱特雷重排反应（Westphalen-Lettré rearrangement）指胆甾烷-3β,5α,6β-三醇二乙酸酯用乙酸酐和硫酸处理时，失去一分子水，在C10-C11间生成双键，并且C10连接的甲基（C19）迁移至C5。[1][2] [3]
反应在过量硫酸存在时对甾类是一级反应。[4] 反应机理可能为首先生成相应的硫酸酯，并在 C5 生成碳正离子，然后再发生重排。
参见
[编辑]参考资料
[编辑]- ^ Theodor Westphalen, Ber., 48, 1064 (1915) doi:10.1002/cber.191504801149
- ^ H. Lettré and I. Muller, Ber., 70, 1947 (1937) doi:10.1002/cber.19370700918
- ^ Rearranged Steroid Systems. I. Studies in the Pregnane Series O. R. RODIG, P. BROWN, and P. ZAFFARONI J. Org. Chem. 1961, 26(7), 2431-2435. (doi: 10.1021/jo01351a066)
- ^ Acid catalysed reactions of 5α-hydroxy-steroids—III : The westphalen rearrangementTetrahedron, Volume 21, Issue 6, 1965, Pages 1567-1580 J. W. Blunt, A. Fischer, M. P. Hartshorn, F. W. Jones, Kirk D. N. and S. W. Yoong (doi:10.1016/S0040-4020(01)98321-8)
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