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Synthesis of Value-Added Intermediates by Continuous Flow Technology

SMITH, LAURA,KATHERINE (2018) Synthesis of Value-Added Intermediates by Continuous Flow Technology. Doctoral thesis, Durham University.

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We present three projects linked by our use of continuous
flow chemistry in the synthesis of organic intermediates. The first is the synthesis of 1,1'-spirobiindane-7,7'-diol (SPINOL) in 6 steps and 32% overall yield. The synthesis has been improved over the previous literature protocols
as it is safer, scalable, and higher-yielding, with better robustness and reproducibility. We introduce two attempts towards the enantioselective synthesis of SPINOL. In the second project, we have developed a flow process based on the Vapourtec reactor to synthesise coumalic acid and
methyl coumalate from malic acid in concetrated sulfuric acid. A new heated rotating flow reactor is also presented for the intensified synthesis of coumalic acid, a valuable intermediate in organic synthesis derived from biorenewable sources of malic acid. Methyl coumalate has been used in two Diels-Alder reactions where the products have applications in molecular electronics and organic light-emitting diodes. Finally, the Darzens
reaction for the synthesis of epoxides is presented here for the first time in flow, providing access to a range of benzaldehyde-derived products, including precursors to the pharmaceutical compound ibuprofen.

Item Type:Thesis (Doctoral)
Award:Doctor of Philosophy
Keywords:organic synthesis; organic chemistry; flow chemistry; process chemistry; process intensification
Faculty and Department:Faculty of Science > Chemistry, Department of
Thesis Date:2018
Copyright:Copyright of this thesis is held by the author
Deposited On:27 Mar 2018 11:21

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