1,2,2-trideuterio-1H-acenaphthylene | 135734-02-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,2-trideuterio-1H-acenaphthylene
• CAS: 135734-02-0
• 化学式: C₁₂H₁₀
• 分子量: 157.188
• InChiKey: CWRYPZZKDGJXCA-XMIJWEOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  甲醇 、 8-(trideuteriomethyl)-1-naphthaldehyde (p-tolylsulfonyl)hydrazone 在 sodium 作用下， 反应 20.0h， 生成 1,2,2-trideuterio-1H-acenaphthylene 、 1-(methoxymethyl)-8-(trideuteriomethyl)naphthalene
  参考文献：
  名称：

  A carbene to biradical rearrangement: reaction paths from (8-methyl-1-naphthyl)carbene to acenaphthene

  摘要：

  Photochemical nitrogen elimination from 1-(diazomethyl)-8-methylnaphthalene (2) yields acenaphthene (3) via the reactive intermediates (8-methyl-1-naphthyl)carbene (a) and 1,8-naphthoquinodimethane (b). The triplet biradical b was observed by absorption spectroscopy at 77 K and by laser flash photolysis at room temperature. The cyclization of triplet b to triplet 3 is forbidden by state symmetry. Two pathways for the reaction b --> 3 have been identified: (1) intersystem crossing to the singlet groud state is rate-determining in the thermal decay of b, and (2) an adiabatic reaction yielding 3 in the lowest excited triplet state was observed upon photolysis of triplet b at 77 K. The carbene precursor of b was intercepted by methanol. This resulted in a reduced yield of transient b in acetonitrile. The trapping reaction did not obey a linear Stern-Volmer relationship.

  DOI：

  10.1021/ja00021a037