Carbamoyl Functionalized Bent para-Phenylenes via an Unexpected Reaction of the Burgess Reagent with α-Ketols.
Sydney N JacksonAndrew L CaskeyNatasha K NarayananBradley L MernerPublished in: The Journal of organic chemistry (2021)
The attempted dehydration of macrocyclic α-ketols with the Burgess reagent has resulted in the unexpected synthesis of carbamoylated, bent para-phenylene units. The same reaction with an acyclic analogue affords the intended dehydration product, indicating that the change in reactivity is conformationally controlled and a result of the bifunctional nature of the Burgess reagent.
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