benzyl p-toluenesulfenate | 10486-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl p-toluenesulfenate
• 英文别名: Benzyl toluene-p-sulphenate；1-methyl-4-phenylmethoxysulfanylbenzene
• CAS: 10486-59-6
• 化学式: C₁₄H₁₄OS
• 分子量: 230.331
• InChiKey: TWRQOESHIJGXGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  351.5±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苄基(对甲苯基)亚砜 以 水 、 叔丁醇 为溶剂， 生成 对甲苯二硫醚 、 4-甲基苯硫代磺酸 S-(4-甲基苯基)酯 、 benzyl p-toluenesulfenate 、 苯甲醛 、 1,2-二苯乙烷 、 苯甲醇
  参考文献：
  名称：

  Photochemistry and Photophysics of Aromatic Sulfoxides. 3. .alpha.-Cleavage and the Role of the Sulfenic Ester

  摘要：

  The photochemistry of aryl benzyl sulfoxides is described. The initial event is homolytic cleavage to form a singlet sulfinyl/benzyl radical pair. This radical pair partitions between reversion to starting material with at least partial racemization and closure to form a sulfenic ester. With acetone sensitization, the primary radical pair also undergoes quite significant escape, leading to formation of diphenylethane and aryl arenethiosulfonates. Secondary photolysis of the sulfenic ester leads exclusively to S-O homolysis, yielding the radical pair from which isolated products are derived. Quantum yields and other mechanistic observations are discussed.

  DOI：

  10.1021/jo00122a029

文献信息

• Photochemistry and Photophysics of Aromatic Sulfoxides. 3. .alpha.-Cleavage and the Role of the Sulfenic Ester
  作者：Yushen Guo、William S. Jenks

  DOI：10.1021/jo00122a029

  日期：1995.9

  The photochemistry of aryl benzyl sulfoxides is described. The initial event is homolytic cleavage to form a singlet sulfinyl/benzyl radical pair. This radical pair partitions between reversion to starting material with at least partial racemization and closure to form a sulfenic ester. With acetone sensitization, the primary radical pair also undergoes quite significant escape, leading to formation of diphenylethane and aryl arenethiosulfonates. Secondary photolysis of the sulfenic ester leads exclusively to S-O homolysis, yielding the radical pair from which isolated products are derived. Quantum yields and other mechanistic observations are discussed.