Attempts to produce novel crowns, incorporating a thioacetal fragment, were made via two synthetic pathways. Despite the well-established reactions found in path A (see figure 3), this method failed to produce the desired crown. Path B, a one-pot reaction originally designed to close rings via the addition of a thioacetal fragment, yielded an oily product that was purified with a silica gel column (48.3% yield). Initial analysis by 1H NMR showed a structure consistent with that of the desired crown (figure 2). Mass spectroscopy was used to verify product identity, confirming the creation of our target molecule 1 ,9-dioxa-4,6-dithiacycloundecane.
Booth, Cassie, "Synthesis of the Novel Crown Ether 1 ,9-Dioxa-4,6-Dithiacycloundecane" (2004). Senior Research Projects. 39.