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Clar Reaction of7H-benz[de]anthracen-7-one: Isolation and Identification of Tetrabenzo[a,cd,lm,o]perylene
Polycyclic Aromatic Compounds ( IF 2.4 ) Pub Date : 2011-06-01 , DOI: 10.1080/10406638.2011.576304
FRANZ S. EHRENHAUSER , MARY J. WORNAT

The Clar reaction of 7H-benz[de]anthracen-7-one (20) was reinvestigated as a source for C34H18 polycyclic aromatic hydrocarbons (PAH). The utilization of a ternary sodium chloride/potassium chloride/zinc chloride melt with zinc dust as reducing agent yielded tetrabenzo[a,cd,j,lm]perylene (11) (10.7% yield), dibenzo[a,cd]naphtho[1,8-jk]perylene (16) (10.2% yield), and dibenzo[a,cd]naphtho[3,2,1-lm]perylene (14) (7.4% yield) as main products. Tetrabenzo[a,cd,lm,o]perylene (26) as a minor product of the Clar reaction was purified via semi-preparative high performance liquid chromatography, and its unequivocal identification was demonstrated through NMR data and a microscale-cyclization reaction.

中文翻译:

7H-benz[de]anthracen-7-one的Clar反应:四苯并[a,cd,lm,o]苝的分离鉴定

7H-benz[de]anthracen-7-one (20) 的 Clar 反应被重新研究为 C34H18 多环芳烃 (PAH) 的来源。利用三元氯化钠/氯化钾/氯化锌熔体和锌粉作为还原剂产生四苯并[a,cd,j,lm]苝(11)(产率10.7%),二苯并[a,cd]萘并[1] ,8-jk]苝(16)(产率10.2%)和二苯并[a,cd]萘并[3,2,1-lm]苝(14)(产率7.4%)作为主要产品。四苯并[a,cd,lm,o]perylene (26) 作为 Clar 反应的次要产物通过半制备型高效液相色谱纯化,其明确的鉴定通过 NMR 数据和微尺度环化反应得到证实。
更新日期:2011-06-01
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