methyl syn-7-bromo-endo-6-iodobicyclo[3.1.1]heptane-exo-6-carboxylate | 1116002-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl syn-7-bromo-endo-6-iodobicyclo[3.1.1]heptane-exo-6-carboxylate
• CAS: 1116002-81-3
• 化学式: C₉H₁₂BrIO₂
• 分子量: 359.002
• InChiKey: XIGKHKYIRYGAQU-AQWKKKTISA-N

反应信息

• 作为产物：
  描述：

  methyl tricyclo[4.1.0.0(2,7)]heptane-1-carboxylate 在 N-碘代丁二酰亚胺 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以43%的产率得到methyl syn-7-bromo-endo-6-iodobicyclo[3.1.1]heptane-exo-6-carboxylate
  参考文献：
  名称：

  Regio-and stereoselectivity in the halogenation of methyl tricyclo[4.1.0.02,7]heptane-1-carboxylate

  摘要：

  Conjugate halogenation of methyl tricyclo[4.1.0.0(2,7)]heptane-1-carboxylate by the action of N-iodoand N-bromosuccinimides in the presence of halide ions occurs exclusively at the central bicyclobutane C-1-C-7 bond via electrophilic attack on the C-1 atom, leading to endo,syn-adducts of the norpinane series. Reactions of the title compound with iodine, dibromotetrachloroethane, and (dichloro-lambda(3)-iodanyl)benzene give not only the corresponding 6,7-endo,syn-dihalonorpinane but also its epimer at C-6, indicating radical mechanism of the halogenation. The regio-and stereoselectivity observed in these ionic and radical reactions are discussed in terms of the results of nonempirical MP2/STO-3G calculations of appropriate cationic and radical intermediates.

  DOI：

  10.1134/s107042800809008x