scholarly journals Pyrene-Based Diarynes as Precursors for Twisted Fused Polycyclic Aromatic Hydrocarbons: A Comparison of Two Routes

2020 ◽  
Vol 02 (04) ◽  
pp. 358-361
Author(s):  
Sven M. Elbert ◽  
Kevin Baumgärtner ◽  
Joshua A. Esteves ◽  
Laura Weber ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Single Crystal ◽  
Aromatic Hydrocarbons ◽  
Diels Alder ◽  
Steric Repulsion ◽  
X Ray ◽  
Polycyclic Aromatic ◽  
End To End ◽  
Helical Chirality

Two bench-stable and readily accessible pyrene-based diaryne precursors based on triflate as well as TMS triflate motifs are introduced and compared in their [4+2]-Diels–Alder reactions with tetracyclone to give an oligophenyl-substituted dibenzo[e,l]pyrene in both cases. By single-crystal X-ray analysis, this twistacene showed helical chirality and an end-to-end contortion of 49.6° due to steric repulsion.

Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds

2019 ◽  
Author(s):  
Evan Darzi ◽  
Joyann Barber ◽  
Neil Garg
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Polycyclic Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbons ◽  
Diels Alder ◽  
Pericyclic Reactions ◽  
One Pot ◽  
Synthetic Strategy ◽  
Polycyclic Aromatic

We report a modular synthetic strategy for accessing heteroatom-containing polycyclic aromatic hydrocarbons (PAHs) that relies on the controlled generation of transient heterocyclic alkynes and arynes. The strained intermediates undergo in situ trapping with readily accessible oxadiazinones. Four sequential pericyclic reactions occur, namely two Diels–Alder / retro-Diels–Alder sequences, which can be performed in a stepwise or one-pot fashion to assemble four new carbon–carbon (C–C) bonds.

Eine PMO-theoretische Untersuchung der benzogenen Diels-Alder-Reaktion polycyclischer aromatischer Kohlenwasserstoffe / APMO-theoretical Treatment of the Benzogenic Diels-Alder Reaction of Polycyclic Arom atic Hydrocarbons

1978 ◽  
Vol 33 (11) ◽  
pp. 1395-1397
Author(s):  
M. Zander
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Maleic Anhydride ◽  
Aromatic Hydrocarbons ◽  
Reaction Rates ◽  
Alder Reaction ◽  
Diels Alder ◽  
Orbital Method ◽  
Theoretical Treatment ◽  
Diels Alder Reaction ◽  
Polycyclic Aromatic

Experimental reaction rates of the benzogenic Diels- Alder reaction of polycyclic aromatic hydrocarbons with maleic anhydride are correlated with the corresponding bislocalization energies calculated by the PMO method. The observed relations between the localization energies of the reacting centres and the topology of the hydrocarbons can be qualitatively understood on the basis of Clar’s π-sextet model of polycyclic systems and Polansky’s pars orbital method.

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