Brian Northrop; Albert Fry; Wallace Pringle
This thesis proves the feasibility of protecting maleimide functionalities with furan via dynamic thermally controlled Diels-Alder cycloaddition reactions, for use in one-pot dendrimer syntheses. Dendrimers up to [G-2] were prepared using the designer monomer compound.
This thesis will also prove, synthetically and computationally, the selective properties of thiol-ene click reactions. N-substituted allyl and propargyl maleimides were prepared and orthogonally reacted with thiols to prove the selectivity of the reactions. Base catalyzed thiol-ene click is selective for electron poor alkenes while the radical-mediated reaction while robust is non-selective. Thus, by utilizing the differences in reactivity, selective thiol-ene can take place by reacting base-catalyzed functionalities prior to radical-mediated addition.
Stolz, Robert Manuel, "Synergy of Dynamic Covalent and Click Methodologies in Dendrimer Synthesis: A Study of Thiol-Ene Reactions in Material Science" (2013). Masters Theses. 41.
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