Electrophilic ‘Umpolung’ Cyclizations of Alkynes in the Synthesis of Polycyclic Aromatic Hydrocarbons
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Polycyclic aromatic hydrocarbons (PAHs), such as acenes and phenacenes, are important structural motifs which have found great utility in the future of electronics as organic semi-conducting materials. Reliable methods of synthesizing PAHs, particularly the phenacene type, are limited; and modern techniques employ expensive transition metal catalysts. A less explored but potentially superior strategy involves utilizing hypervalent iodine methodology, avoiding the need for transition metal catalysts. In recent studies, a reaction was developed that could couple ortho-biphenylstyrenes intramolecularly in the synthesis of phenanthrenes using only a catalytic amount of iodotoluene, and m-CPBA as an oxidant. In this thesis, we investigate the mechanism of the rearrangement observed in this recently uncovered reaction, and further apply what we have learned toward a novel strategy for electrophilic ‘umpolung’ cyclizations of alkynes in the synthesis of fluorinated PAHs.
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Liam Britt (2021). Electrophilic ‘Umpolung’ Cyclizations of Alkynes in the Synthesis of Polycyclic Aromatic Hydrocarbons. UWSpace. http://hdl.handle.net/10012/16971