benzaldehyde O-oxide | 78894-20-9

• 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: benzaldehyde O-oxide
• 英文别名: Benzylidene(oxido)oxidanium
• CAS: 78894-20-9
• 化学式: C₇H₆O₂
• 分子量: 122.123
• InChiKey: HOPCGGVVBWWGTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 在 吡啶 、 氧气 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 生成 benzaldehyde O-oxide
  参考文献：
  名称：

  苯亚甲基作为环氧化苯乙烯酸催化氧化的中间体

  摘要：

  在对甲苯磺酸 (MeCN, ButOH (90 vol.%) + 氯苯 (10 vol.%) + 氯苯 (10 vol.%) 的影响下，在环氧化苯乙烯的酸催化消耗条件下，已经记录了亚胺鎓盐 (λmax = 450 nm) 的吸收光谱。 %), 343 K) 在吡啶存在下。该光谱与吡啶与苯亚甲基的苯卡宾相互作用的叶立德产物的光谱一致，在从重氮衍生物制备卡宾的常规闪光光解制备中形成。结果证实了先前关于在环氧-酸体系中与氧反应形成卡宾性质的颗粒的假设。在没有 O2 的情况下，这些颗粒会破坏引入的氢过氧化物。在乙腈中记录存在和不存在吡啶时相应羰基氧化物的光谱 (λmax ≈ 408, 400 nm)。

  DOI：

  10.1007/s11172-016-1605-7

文献信息

• Mechanistic Study on the Reaction of Phenyldiazomethanes with Singlet Oxygen:  Formation and Cycloreversion of 1,2,3,4-Dioxadiazole Intermediates
  作者：Takayuki Nojima、Katsuya Ishiguro、Yasuhiko Sawaki

  DOI：10.1021/jo9711394

  日期：1997.10.1

  The formation of carbonyl oxides in the singlet oxygen (O-1(2)) oxidation of phenyldiazomethanes 1 has been investigated mechanistically. Product ratios of N-2/N2O, which are indicative of the selectivity in the carbonyl oxide/ketone formation, were determined by gas chromatography/mass spectrometry (GC/MS). The yields of carbonyl oxides were not affected by changing solvents but were significantly increased with the increasing electron-donating ability of substituents on diazomethanes. Rate constants for the quenching of O-1(2) by 1 as determined by monitoring the emission of O-1(2) at 1270 nm were also insensitive to solvents. These results suggest the predominant formation of 1,2,3,4-dioxadiazole intermediates by the cycloaddition of O-1(2) to 1 followed by its cycloreversion, the selectivity of which is controlled by the relative stability of resulting carbonyl oxides. The formation of carbonyl oxides, observable from its transient absorption at similar to 400 nm, was in good agreement with the decay of O-1(2) within the experimental error, indicating that the 1,2,3,4-dioxadiazoles are a highly labile intermediate with the lifetime of less than 100 ns.