Diels−Alder Reactivity of Polycyclic Aromatic Hydrocarbon Bay Regions: Implications for Metal-Free Growth of Single-Chirality Carbon Nanotubes

2009 ◽  
Vol 131 (44) ◽  
pp. 16006-16007 ◽  
Author(s):  
Eric H. Fort ◽  
Patrick M. Donovan ◽  
Lawrence T. Scott
Keyword(s):  
Carbon Nanotubes ◽  
Polycyclic Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbon ◽  
Diels Alder ◽  
Metal Free ◽  
Polycyclic Aromatic ◽  
Free Growth

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.

scholarly journals Diels-Alder Additions to 2,2’-Biaceanthrylene

2021 ◽  
Author(s):  
Yachu Du ◽  
Kyle Plunkett
Keyword(s):  
Polycyclic Aromatic Hydrocarbon ◽  
Aromatic Hydrocarbon ◽  
Photophysical Properties ◽  
Major Product ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Polycyclic Aromatic ◽  
Single Addition ◽  
Quinone Derivative

A series of Diels-Alder reactions between the diene 2,2’-biaceanthylene and several dienophiles is presented. The diene is a cyclopenta-fused polycyclic aromatic hydrocarbon with anthracene units linked by two cyclopentene rings. Depending on the dienophile, the major product was the result of a single addition (dimethyl acetylenedicarboxylate) or double addition (quinone, benzyne) to the diene. Single crystal X-ray analysis of the quinone-derivative shows a propeller-like structure composed of mixed enantiomers. The synthesis and photophysical properties of these compounds is presented.<br>

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.

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