m-nitrobenzenesulfonyl peroxide | 6209-71-8

• 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: m-nitrobenzenesulfonyl peroxide
• 英文别名: Bis-<3-nitro-benzolsulfonyl>-peroxid；Bis-(3-nitrobenzolsulfonyl)-peroxid；m-Nitrophenyl-sulfonylperoxyd；m-Nitrobenzolsulfonylperoxid；m-Nitrophenylsulfonylperoxid；(3-nitrophenyl)sulfonyloxy 3-nitrobenzenesulfonate
• CAS: 6209-71-8
• 化学式: C₁₂H₈N₂O₁₀S₂
• 分子量: 404.335
• InChiKey: HTFPLYQUBPPUPL-UHFFFAOYSA-N

物化性质

• 熔点：
  107 °C (decomp)
• 沸点：
  594.4±60.0 °C(Predicted)
• 密度：
  1.704±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  m-nitrobenzenesulfonyl peroxide 以 氯仿 为溶剂， 反应 168.0h， 以95%的产率得到3-硝基苯磺酸水合物
  参考文献：
  名称：

  The use of sulfur-33 chemical shifts to determine pKa's of arenesulfonic acids

  摘要：

  DOI：

  10.1021/jo00375a051
• 作为产物：
  描述：

  3-硝基苯磺酰氯 在 双氧水 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 m-nitrobenzenesulfonyl peroxide
  参考文献：
  名称：

  Arylsulfonoxylation of aromatic compounds. II. Partial rate factors for the nitrophenylsulfonoxylation of alkylbenzenes

  摘要：

  DOI：

  10.1021/jo00834a045
• 作为试剂：
  描述：

  苯乙烯 、 二苯基二硒醚 在 sodium azide 、 m-nitrobenzenesulfonyl peroxide 作用下， 生成 (2-azido-2-phenylethyl)(phenyl)selane
  参考文献：
  名称：

  Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process

  摘要：

  A simple and mild azido-phenylselenenylation of terminal alkenes, which proceeds with complete anti-Markovnikov regioselectivity, has been developed. This reaction occurs when the alkenes are treated with (diacetoxyiodo)benzene, sodium azide, and diphenyl diselenide in dichloromethane at room temperature. The observed regioselectivity can be explained by assuming that the addition process is initiated by azido radicals. This was further supported by the results obtained starting from 1,6-heptadiene and from beta-pinene. Under the same conditions, efficient azido-phenylselenenylation of symmetrical olefins, 3,4-dihydro-2H-pyran, methyl acrylate, and vinyl crotonate can also be effected.

  DOI：

  10.1021/jo00024a020

文献信息

• Oxidative Cleavage of Diselenide by<i>m</i>-Nitrobenzenesulfonyl Peroxide. Novel Method for the Electrophilic Benzeneselenenylations of Olefins and Aromatic Rings
  作者：Masato Yoshida、Shuichi Sasage、Kyoko Kawamura、Takashi Suzuki、Nobumasa Kamigata

  DOI：10.1246/bcsj.64.416

  日期：1991.2

  acetic acid, phenol, and anisole could be employed; oxyselenenylated ((Remark: Graphics omitted.) : R=H, Me, Ac, and Ph) and arylselenenylated ((Remark: Graphics omitted.) : R=H and Me) adducts were afforded. Phenol gave oxyselenenylated products in cyclohexene or 1-octene and arylselenenylated products in styrene. Efficient intramolecular cyclizations of unsaturated alcohols and carboxylic acids were

  发现二苯基二硒化物通过用间硝基苯磺酰过氧化物处理很容易转化为间硝基苯磺酸苯硒基酯 (PhSeOSO2C6H4NO2-m)。当如此形成的硒基磺酸盐在各种亲核试剂的存在下与烯烃如环己烯、1-辛烯或苯乙烯原位反应时，得到苯硒基基团和亲核试剂的加合物。亲核试剂水、甲醇、乙酸、苯酚和苯甲醚均可使用；得到氧硒烯化（（备注：省略图示。）：R=H、Me、Ac 和 Ph）和芳​​基硒酰化（（备注：图示省略。）：R=H 和 Me）加合物。苯酚在环己烯或 1-辛烯中生成氧化硒化产物，在苯乙烯中生成芳基硒化产物。不饱和醇和羧酸的有效分子内环化同样通过磺酸硒进行，得到相应的苯硒化环醚和内酯。硒基磺酸盐也被发现是一种高...
• Novel preparation of highly electrophilic species for benzenetellurenylation or benzenesulfenylation by nitrobenzenesulfonyl peroxide in combination with ditelluride or disulfide. Application to intramolecular ring closures
  作者：Masato Yoshida、Takashi Suzuki、Nobumasa Kamigata

  DOI：10.1021/jo00027a068

  日期：1992.1
• Reactions of N-(arylsulfonoxy)-N-benzylmethylamines with sodium methoxide in methanol
  作者：Bong Rae Cho、Sang Yong Pyun、Tae Rin Kim

  DOI：10.1021/ja00260a015

  日期：1987.12
• Convenient preparations and Michael reactions of 4-fluoroalkylated but-2-en-4-olides
  作者：Masato Yoshida、Rihoko Imai、Yuji Komatsu、Yoshihiro Morinaga、Nobumasa Kamigata、Masahiko Iyoda

  DOI：10.1039/p19930000501

  日期：——

  Trifluoromethyl, heptafluoropropyl and chlorodifluoromethyl substituted but-2-en-4-olides have been prepared both from 2-trimethylsiloxyfuran by fluoroalkylation with the corresponding bis(fluoroalkanoyl) peroxide and from 2-fluoroalkylfuran by oxidation with m-nitrobenzenesulfonyl peroxide. 4-Difluoromethylbut-2-en-4-olide was also prepared by chlorodifluoromethylation of 2-methoxy-furan followed by reduction of the chlorine. The 4-trifluoromethylated butenolide, thus prepared, could be readily converted into the anion by treatment with weak base. The anion so formed then reacted with electron-deficient olefins to give 4,4-disubstituted butenolides.
• YOSHIDA, MASATO;MOCHIZUKI, HIDEKI;KAMIGATA, NOBUMASA, CHEM. LETT.,(1988) N2, C. 2017-2020
  作者：YOSHIDA, MASATO、MOCHIZUKI, HIDEKI、KAMIGATA, NOBUMASA

  DOI：——

  日期：——