Aromatische Kohlenwasserstoffe LXXVIII. Höher Kondensierte Pyrene

Abstract

Die Anellierungsreihe Naphthalin, Pyren, 1.12‐Benzperylen wird durch die Synthese der Kohlenwasserstoffe III, VIII und XI fortgesetzt. Die Spektren dieser Reihe werden verglichen mit denen der Reihe Benzol, Naphthalin, Chrysen, Picen. Der Kohlenwasserstoff I wird durch Kondensation von Pyren mit 1‐Bromnaphthalin und Aluminiumchlorid dargestellt. Mit Maleinsäureanhydrid wird daraus über die Dicarbonsäure II der Kohlenwasserstoff III dargestellt. 3.3'‐Dipyrenyl (V) aus 3‐Brompyren und Kupferpulver ist identisch mit einem bereits früher auf anderem Wege erhaltenen Produkt. Sein Ringschluß ergibt VI, daraus gewinnt man mit Maleinsäureanhydrid VII und durch Decarboxylierung VIII. Zweifache Kondensation von Pyren mit Bromnaphthalin gibt den blauen Kohlenwasserstoff IX, der zweimal Maleinsäureanhydrid zu X addiert, dessen Decarboxylierung XI liefert.

Additivity of resonance energy in benzenoid hydrocarbons

“…Starphenes and the series of hydrocarbons annellated in a zig-zag way lie above the line. In the latter two cases the .rr-electron transport is more complicated and less efficient than in the acene or phene series [12].…”

π-Conjugated Benzoperylenes: Sequential C–S Bond Cleavage and Charge Distribution Patterns of the Anions

“…Cyclization of 7 was achieved in the using semiemperical methods, [21] it is clear that only a small melt in the presence of sodium chloride and aluminum charge resides on the sulfur atom. While most of the carbon chloride [18] to afford 2,4:9,11-dinaphthoperylene (8) [19] in atoms carry small charge densities with δ 13 C ranging from 60% yield.…”

Bottom‐up Approaches to Nanographenes through Organic Synthesis

“…More recently, Fujisawa et al prepared compound 52 following a procedure initiated by an Ullmann coupling [42]. Dibenzobisanthenes 55 and 56 were originally synthesized from 6-and 8-chlorobenzanthrones [43], while compound 57 was obtained by the synthetic route shown in Scheme 11.9 [33]. Dibenzobisanthenes 55 and 56 were originally synthesized from 6-and 8-chlorobenzanthrones [43], while compound 57 was obtained by the synthetic route shown in Scheme 11.9 [33].…”

“…Diels-Alder reaction with maleic anhydride in the presence of chloranil as a dehydrogenating agent followed by decarboxylation with soda lime [Ca(OH) 2 , NaOH, KOH, H 2 O] at high temperature led to compound 57 [33]. Diels-Alder reaction with maleic anhydride in the presence of chloranil as a dehydrogenating agent followed by decarboxylation with soda lime [Ca(OH) 2 , NaOH, KOH, H 2 O] at high temperature led to compound 57 [33].…”

“…Tetrabenzopyranthrene 97 was isolated as a by-product in the reductive dimerization of phenalenone 74 [49a]. Tetrabenzopyranthrene 99 was prepared by Clar and Kühn from polyarene 41 through Diels-Alder reactions with maleic anhydride followed by decarboxylation [33]. Tetrabenzopyranthrene 99 was prepared by Clar and Kühn from polyarene 41 through Diels-Alder reactions with maleic anhydride followed by decarboxylation [33].…”