3:4,15:16-Dibenzopentacyclo[5.5.2.2^2,5.0^1,6.0^6,10]hexadeca-3,8,11,13,15-pentaene | 212195-06-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 3:4,15:16-Dibenzopentacyclo[5.5.2.2^2,5.0^1,6.0^6,10]hexadeca-3,8,11,13,15-pentaene
• CAS: 212195-06-7
• 化学式: C₂₄H₁₈
• 分子量: 306.407
• InChiKey: BARHQDUCWBWDRN-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  3:4,15:16-Dibenzopentacyclo[5.5.2.2^2,5.0^1,6.0^6,10]hexadeca-3,8,11,13,15-pentaene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 氘代苯 为溶剂， 反应 1.0h， 生成 7-Bromo-3:4,15:16-dibenzopentacyclo[5.5.2.2^2,5.0^1,6.0^6,10]hexadeca-3,8,11,13,15-pentaene
  参考文献：
  名称：

  Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives

  摘要：

  A versatile approach towards the highly strained acepentalene 3 via the readily accessible dipotassium acepentalenediide (10a) and the highly strained tetraenes 7 is reported, An unexpected [4+2] cycloaddition dimer 14 is formed upon protonation of the dipotassium acepentalenediide (10a) in 93% yield, and the monomeric 4,7-dihydroacepentalene (7a), as the reactive intermediate, can be trapped with anthracene to form the corresponding Diels-Alder adduct 16 in 15% yield. In contrast, the highly strained, but sterically protected monomeric bridgehead-bridgehead alkenes 7c,d can be isolated upon reaction of 10a or 10b with bulkli electrophiles, such as Me-3-SiCl and Me3SnCl, respectively. The X-ray crystal structure analysis of 7d exhibits a highly pyramidalized central double bond. The bisstannane 7d is an ideal precursor for acepentalene (3) which would be formed by removal of the two trimethylstannyl substituents. It can also be transmetallated to give the pure crystalline dilithium acepentalenediide (10b) in 78% yield. According to its H-1, Li-7 and C-13 NMR spectra, the bowl-shaped 12 pi-dianion in 10b is an aromatic species, and it undergoes a rapid bowl-to-bowl inversion at room temperature.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1192::aid-chem1192>3.0.co;2-g
• 作为产物：
  描述：

  蒽 、 Dipotassium acepentalenediide 在 水 作用下， 以 四氢呋喃 、 苯 为溶剂， 以18%的产率得到Heptacyclo[11.5.2.0^1,12.0^2,10.0^4,11.0^7,11.0^12,16]eicosa-3,5,8,14,17,19-hexaene
  参考文献：
  名称：

  Syntheses, Structures, and Reactions of Highly Strained Dihydro- and Tetrahydroacepentalene Derivatives

  摘要：

  A versatile approach towards the highly strained acepentalene 3 via the readily accessible dipotassium acepentalenediide (10a) and the highly strained tetraenes 7 is reported, An unexpected [4+2] cycloaddition dimer 14 is formed upon protonation of the dipotassium acepentalenediide (10a) in 93% yield, and the monomeric 4,7-dihydroacepentalene (7a), as the reactive intermediate, can be trapped with anthracene to form the corresponding Diels-Alder adduct 16 in 15% yield. In contrast, the highly strained, but sterically protected monomeric bridgehead-bridgehead alkenes 7c,d can be isolated upon reaction of 10a or 10b with bulkli electrophiles, such as Me-3-SiCl and Me3SnCl, respectively. The X-ray crystal structure analysis of 7d exhibits a highly pyramidalized central double bond. The bisstannane 7d is an ideal precursor for acepentalene (3) which would be formed by removal of the two trimethylstannyl substituents. It can also be transmetallated to give the pure crystalline dilithium acepentalenediide (10b) in 78% yield. According to its H-1, Li-7 and C-13 NMR spectra, the bowl-shaped 12 pi-dianion in 10b is an aromatic species, and it undergoes a rapid bowl-to-bowl inversion at room temperature.

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1192::aid-chem1192>3.0.co;2-g