Attempted synthesis of aromatic belts

Yu, Hao (2004) Attempted synthesis of aromatic belts. Masters thesis, Memorial University of Newfoundland.

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Abstract

In this thesis, the synthesis of a molecular board, which is a potential precursor to some aromatic belts, will be described. -- The first synthetic approach to the molecular board in which IEDDA (inverse electron demand Diels-Alder) chemistry is involved will be discussed in Chapter 2. This approach did not lead to the formation of the molecular board due to the failure of the formation of the C-C bond between benzylic carbons. Direct alkylation and variations of Wittig reaction were employed in this approach. -- The second synthetic approach that involved Sonogashira coupling successfully constructed the main body of the molecular board. A Pd-catalyzed intramolecular arylation, which is the key step in this synthesis, gave rise to the molecular board. -- Further investigation of converting this molecular board into corresponding aromatic belts has not met with the success due to the serious solubility problem. Future work should be directed into this concern.

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