| 145325-97-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 145325-97-9
• 化学式: C₁₁H₁₆Br₂O₂
• 分子量: 340.055
• InChiKey: VRYMYBBMLKYVLI-YDYPAMBWSA-N

反应信息

• 作为反应物：
  描述：

  在 硫酸 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 15.08h， 生成 <4,5>dihomotropone
  参考文献：
  名称：

  Is Through-Bond Dihydroaromaticity Attainable? Preparation of [4,5]Dihomotropone, Investigation of Its Ground-State Properties, and an Attempt to Generate the Dihomotropylium Cation

  摘要：

  Construction of the first dihomotropone (6) has been accomplished. The key elements of the synthesis were a regiocontrolled expansion of a [4.1.1] bicyclic cr-bromo ketone and introduction of the dienone double bonds by means of the Garbisch method. The spectral properties of 6 under neutral and strongly acidic conditions are described and interpreted in terms of a lack of dihomoaromatic character. The parent bicyclo[5.1.1]nonadienyl cation is unstable and experiences ready Wagner-Meerwein rearrangement to the bicyclo[4.2.1]nonadien-7-yl cation. These features appear well suited to the ultimate evaluation of through-bond interaction in tricyclic homologues of 6 that carry perpendicular pi arrays in the third ring.

  DOI：

  10.1021/jo00098a031
• 作为产物：
  描述：

  Bicyclo<5.1.1>nonan-4-one ethylene ketal 在 溴 作用下， 以 乙二醇 为溶剂， 反应 0.33h， 以82%的产率得到
  参考文献：
  名称：

  Is Through-Bond Dihydroaromaticity Attainable? Preparation of [4,5]Dihomotropone, Investigation of Its Ground-State Properties, and an Attempt to Generate the Dihomotropylium Cation

  摘要：

  Construction of the first dihomotropone (6) has been accomplished. The key elements of the synthesis were a regiocontrolled expansion of a [4.1.1] bicyclic cr-bromo ketone and introduction of the dienone double bonds by means of the Garbisch method. The spectral properties of 6 under neutral and strongly acidic conditions are described and interpreted in terms of a lack of dihomoaromatic character. The parent bicyclo[5.1.1]nonadienyl cation is unstable and experiences ready Wagner-Meerwein rearrangement to the bicyclo[4.2.1]nonadien-7-yl cation. These features appear well suited to the ultimate evaluation of through-bond interaction in tricyclic homologues of 6 that carry perpendicular pi arrays in the third ring.

  DOI：

  10.1021/jo00098a031

文献信息

• Synthesis and properties of [4,5]dihomotropone (bicyclo[5.1.1]Nona-2,5-dien-4-one)
  作者：Loe A. Paquette、Eric Bacqué、Roger Bishop、Timothy J. Watson

  DOI：10.1016/s0040-4039(00)60984-x

  日期：1992.10

  The potentially through-bond "dihomoaromatic" title compound has been elaborated by means of a tandem acyloin-ring expansion sequence and shown by spectroscopic means not to possess significant ground-state polarization.