Natural receptors such as an enzyme with an inwardly directed functional group serving as well-organized chemical catalysts. New supramolecular cavitands that contain inwardly directed functional groups have also yielded specialized transformations and trapping of reactive intermediates. A newly reported 3-wall Au cavitand could provide new opportunities for supramolecular catalysis and the study of reactive intermediates. In our study, a variety of intramolecular reactions are examined to explore the effect of the cavitands on chemical reactivity. Alkyne-acids with different spectator groups are expected to result in differential catalyst behavior. We obtained 5-membered ring cyclization products from alkyne-acids. Smaller spectator groups gave a better percentage of conversion. However, the presence of benzyl group resulted in lower percent conversion. We propose that the benzyl group binds inside the cavitand and somehow inhibits cyclization. Solvents and temperature also affect the outcome of these reactions. These results will give insight into how cavitands can be used towards new chemical challenges.

Intramolecular reactions of alkyne-acids using a gold functionalized cavitand

256th National Meeting (2018)

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