Synthesis of thioenol ether functionalized cyclooctyne and its orthogonal cycloaddition sequence

Vaccari, Thomas (2020) Synthesis of thioenol ether functionalized cyclooctyne and its orthogonal cycloaddition sequence. [Laurea magistrale], Università di Bologna, Corso di Studio in Chimica industriale [LM-DM270]
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In this work, the synthesis of a new bifunctionalized cyclooctyne for a possible layer by layer surface functionalization is presented. The main objective is to find a more stable molecule than the literature known methyl enol ether substituted cyclooctyne. Accordingly, the two target functionalities are an internal alkyne group and a vinyl methyl sulfide group. The synthesis was achieved in 9 steps and consists first of all in the preparation of an aldehyde starting from 1,5-cyclooctadiene with a cyclopropanation reaction followed by a reduction and the SWERN oxidation to an aldehyde. The new functionality was introduced by exploiting the WITTIG reaction. For the alkyne group a bromination followed by a double elimination gave good results. The reactivity of the new molecule was tested using a sequential application of SPAAC and iEDDA reactions, comparing it with the cyclooctyne functionalized with a methyl enol ether. Concerning the comparison of both compounds the sulfur ether is significantly slower and therefore more stable. It will be tested in the future for surface functionalization from the KOERT group.

Tipologia del documento
Tesi di laurea (Laurea magistrale)
Autore della tesi
Vaccari, Thomas
Relatore della tesi
Correlatore della tesi
Corso di studio
Ordinamento Cds
Parole chiave
cyclooctyne SPAAC iEDDA multilayer Swern oxidation Wittig reaction click chemistry
Data di discussione della Tesi
19 Ottobre 2020

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