endo-6,syn-7-dichloro-exo-6-methylsulfonylbicyclo-[3.1.1]heptane | 1374126-41-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: endo-6,syn-7-dichloro-exo-6-methylsulfonylbicyclo-[3.1.1]heptane
• CAS: 1374126-41-6
• 化学式: C₈H₁₂Cl₂O₂S
• 分子量: 243.154
• InChiKey: ZYJQCTNRFBQGFP-WZQOZDJLSA-N

反应信息

• 作为产物：
  描述：

  endo-6,syn-7-dibromo-exo-6-methylsulfonylbicyclo-[3.1.1]heptane 在 (二氯碘)-苯 、 potassium tert-butylate 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 endo-6,syn-7-dichloro-exo-6-methylsulfonylbicyclo-[3.1.1]heptane
  参考文献：
  名称：

  Products and mechanism of some halogenation reactions of 1-sulfonyl-substituted tricyclo[4.1.0.02,7]heptanes

  摘要：

  Reactions of 1-methylsulfonyl- and 1-phenylsulfonyltricyclo[4.1.0.0(2,7)]heptanes with iodine, dioxane dibromide, and dichloro-lambda(3)-iodanylbenzene (under irradiation) gave products of stereoselective syn addition of halogen at the C-1-C-7 central bicyclobutane bond. 7-Methyl-1-phenylsulfonyltricyclo[4.1.0.0(2,7)]- heptane reacted with dioxane dibromide in carbon tetrachloride to produce a mixture of 2-bromo- and 2,3-di- bromo-1-methyl-exo-7-phenylsulfonylnorcaranes at a ratio of 1 : 4 as a result of cleavage of the C-1-C-2 bicyclobutane bond. 7-Bromo- and 7-methoxycarbonyl-1-phenylsulfonyltricyclo[4.1.0.0(2,7)] heptanes take up bromine exclusively at the C-1-C-7 central bond with strict syn stereoselectively. The regio- and stereoselectivity of the addition and their relations with the halogen nature were interpreted with account taken of structural specificities of intermediate 6-sulfonyl-substituted 6-norpinanyl radicals determined by ab initio quantum-chemical calculations using 6-31G basis set.

  DOI：

  10.1134/s1070428012030049