N-bromoformamide | 3699-16-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-bromoformamide
• 英文别名: N-Brom-formamid；N-bromo carboxylic acid amide；N-bromocarboxamide
• CAS: 3699-16-9
• 化学式: CH₂BrNO
• 分子量: 123.937
• InChiKey: WSSOFBRSFAPKKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  4
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-bromoformamide 、 环己烯 在 chromium dichloride 作用下， 以14%的产率得到N-(2-bromocyclohexyl)formamide
  参考文献：
  名称：

  Photolytic and chromium(II)-promoted addition reactions of N-halogenoformamides with alkenes

  摘要：

  Formamidyl radicals (HCONR) do not intramolecularly abstract hydrogen or cyclise onto aromatic rings, but do add intermolecularly to alkenes. The photolytic addition of N-halogenoformamides to alkenes is inhibited by N-alkylation. However, N-alkyl-N-halogenoformamides add to alkenes in the presence of chromium(II) species. The addition of N-halogenoformamides to alkenes occurs regiospecifically with formamidyl bonding to the less substituted terminus of the alkene. The adducts obtained from N-alkylformamidyls exist as mixtures of rotameric isomers whose configurations have been assigned. The reactivity of the formamidyl radical has been discussed in terms of its conformation and electronic state.

  DOI：

  10.1039/p19920000627
• 作为产物：
  描述：

  formamide 在 sodium bromate 、 硫酸 、 氢溴酸 作用下， 以 水 为溶剂， 反应 0.5h， 以48%的产率得到N-bromoformamide
  参考文献：
  名称：

  使用溴酸钠的有机合成。二、在硫酸存在下使用溴酸钠和氢溴酸（或溴化钠）简便合成 N-溴酰亚胺和酰胺

  摘要：

  在温和条件下，在硫酸存在下，酰亚胺和酰胺在水（或乙酸水溶液）中与溴酸钠和氢溴酸（或溴化钠）反应，以高产率得到相应的 N-溴化物。

  DOI：

  10.1246/bcsj.66.2426

文献信息

• Organic Synthesis Using Sodium Bromate. II. A Facile Synthesis of<i>N</i>-Bromo Imides and Amides Using Sodium Bromate and Hydrobromic Acid (or Sodium Bromide) in the Presence of Sulfuric Acid
  作者：Shizuo Fujisaki、Satoshi Hamura、Hisao Eguchi、Akiko Nishida

  DOI：10.1246/bcsj.66.2426

  日期：1993.8

  The reaction of imides and amides in water (or aqueous acetic acid) with sodium bromate and hydrobromic acid (or sodium bromide) in the presence of sulfuric acid under mild conditions gave the corresponding N-bromides in high yields.

  在温和条件下，在硫酸存在下，酰亚胺和酰胺在水（或乙酸水溶液）中与溴酸钠和氢溴酸（或溴化钠）反应，以高产率得到相应的 N-溴化物。
• Boismenu, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1911, vol. 153, p. 679,950,1484
  作者：Boismenu

  DOI：——

  日期：——
• Photolytic and chromium(II)-promoted addition reactions of N-halogenoformamides with alkenes
  作者：Andr� Goosen、Cedric W. McCleland、Alan J. Merrifield

  DOI：10.1039/p19920000627

  日期：——

  Formamidyl radicals (HCONR) do not intramolecularly abstract hydrogen or cyclise onto aromatic rings, but do add intermolecularly to alkenes. The photolytic addition of N-halogenoformamides to alkenes is inhibited by N-alkylation. However, N-alkyl-N-halogenoformamides add to alkenes in the presence of chromium(II) species. The addition of N-halogenoformamides to alkenes occurs regiospecifically with formamidyl bonding to the less substituted terminus of the alkene. The adducts obtained from N-alkylformamidyls exist as mixtures of rotameric isomers whose configurations have been assigned. The reactivity of the formamidyl radical has been discussed in terms of its conformation and electronic state.