2-fluoro-6-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide | 136859-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-fluoro-6-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide
• CAS: 136859-48-8
• 化学式: C₁₃H₁₀FNO₂S
• 分子量: 263.292
• InChiKey: WAPLFDIGEFPVSC-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  4-氟苯磺酰氯 在 偶氮二异丁腈 、 1,1,2,2-tetraphenyldisilane 、 三乙胺 作用下， 以 间二甲苯 为溶剂， 反应 22.0h， 生成 2-fluoro-6-methyl-6H-dibenzo[c,e][1,2]thiazine-5,5-dioxide
  参考文献：
  名称：

  Synthetic use of 1,1,2,2-tetraphenyldisilane for the preparation of biaryls through the intramolecular free radical ipso-substitution of N-(2-bromoaryl)arenesulfonamides

  摘要：

  Treatment of various N-methyl-N-(2-bromoaryl)arenesulfonamides (1a-g, 1i, and 1m) with 1,1,2,2-tetraphenyldisilane and AIBN under heating conditions gave the corresponding biaryl products (2a-g, 2i, and 2m) in moderate yields through the intramolecular radical ipso-substitution. However, N-H foe N-(2-brornoaryl)arenesulfonamides Ih and 2-bromoaryl arenesulfonate 1j did not give the corresponding biarys. 1,1,2,2-Tetraphenyldisilane is the most effective reagent for 1,5-ipso-substitution on the sulfonamides among typical radical reagents such as diphenylsilane, tributyltin hydride, tris(trimethylsilyl)silane, and 1,1,2,2-tetraphenyldisilane. Furthermore, 1,1,2,2 tetraphenyldisilane has the advantages of low toxicity, stability, and ease of preparation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00560-9

文献信息

• Synthesis of biaryls via intramolecular free radical ipso-substitution reactions
  作者：Feroze Ujjainwalla、Maria Lucília E.N. da Mata、Andrew M.K. Pennell、Carmen Escolano、William B. Motherwell、Santiago Vázquez

  DOI：10.1016/j.tet.2015.07.048

  日期：2015.9

  intramolecular free radical [1,5]-ipso-substitution using sulfonamide and sulfonate derived tethering chains. The overall efficiency of the process is determined by appropriately positioned substituents on the aromatic acceptor ring. The extension of the process to benzylic sulfonates and their corresponding N-methylsulfonamide alternatives as substrates in potential [1,6]-ipso-substitution reactions leads

  使用磺酰胺和磺酸酯衍生的束缚链，通过分子内自由基[1,5] -ipso取代制备各种官能化的联芳基和杂联芳基。该方法的总效率由芳族受体环上适当定位的取代基决定。该方法的扩展来苄基磺酸酯和它们的相应Ñ -methylsulfonamide替代作为底物在潜在[1,6] -本位3'-取代反应引线主要以替代[1,7]加成产物。
• A novel route to biaryls via intramolecular free radical ipso substitution reactions
  作者：William B. Motherwell、Andrew M. K. Pennell

  DOI：10.1039/c39910000877

  日期：——

  A variety of usefully functionalised biaryls may be prepared under neutral conditions by an intramolecular free radical ipso substitution reaction at an sp2 sulphonyl substituted carbon atom; the overall efficiency of the process being determined both by the nature and number of atoms linking the two aromatic rings and by appropriately positioned substituents on the aromatic aceeptor ring.

  可以在中性条件下通过sp 2磺酰基取代的碳原子上的分子内自由基ipso取代反应制备各种有用的官能化联芳基；该方法的总效率取决于连接两个芳环的原子的性质和数量以及芳族乙酰对映体环上适当放置的取代基。