(2β,4aα,8aβ)-Octahydro-4a-methyl-8a-(trimethyl)stannylspiro | 131905-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2β,4aα,8aβ)-Octahydro-4a-methyl-8a-(trimethyl)stannylspiro
• CAS: 131905-53-8
• 化学式: C₁₅H₂₈OSn
• 分子量: 343.097
• InChiKey: PCFRLTIYUMRVNY-RDKDOERDSA-N

反应信息

• 作为反应物：
  描述：

  (2β,4aα,8aβ)-Octahydro-4a-methyl-8a-(trimethyl)stannylspiro 在 二氯乙基铝 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到cis-2,3,4,4a,5,6,7,8-octahydro-4a-methyl-2-naphthalenemethanol
  参考文献：
  名称：

  1,3-Elimination reactions of (3,4-epoxybutyl)stannanes. Approach to the synthesis of cycloeudesmol

  摘要：

  The reactions that occur when stereochemically defined spirocyclic (3,4-epoxybutyl)stannanes are treated with C2H5AlCl2 depend critically on the relative orientation of tin, oxygen, and the three connecting atoms of carbon. A W arrangement of these atoms tends to favor formation of cyclopropanes by a concerted 1,3-elimination with inversion at both carbon centers. If this orientation cannot be achieved, cleavage of the epoxide occurs to give an ionic intermediate that can undergo a subsequent 1,3-elimination or a 1,2-shift of hydride promoted by an antiperiplanar carbon-tin bond.

  DOI：

  10.1021/jo00006a019