exo-6,syn-7-dibromo-endo-6-methylsulfonylbicyclo-[3.1.1]heptane | 1374156-12-3

• 分子结构分类: 有机化合物
• 英文名称: exo-6,syn-7-dibromo-endo-6-methylsulfonylbicyclo-[3.1.1]heptane
• CAS: 1374156-12-3
• 化学式: C₈H₁₂Br₂O₂S
• 分子量: 332.056
• InChiKey: AIFKNTPOUDEXSG-SOSBWXJGSA-N

反应信息

• 作为产物：
  描述：

  endo-6,syn-7-dibromo-exo-6-methylsulfonylbicyclo-[3.1.1]heptane 在 potassium tert-butylate 、 溴-1,4-二氧六环复合物 、 calcium carbonate 作用下， 以 四氯化碳 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 syn-7-dibromo-exo-6-methylsulfonylbicyclo-[3.1.1]heptane 、 exo-6,syn-7-dibromo-endo-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