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Bis(1-cyanovinyl acetate) Is a Linear Precursor to 3‑Oxidopyrylium Ions

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posted on 14.10.2016, 00:00 authored by Sidney Malik Wilkerson-Hill, Shota Sawano, Richmond Sarpong
Herein we describe the first approach to 3-oxidopyrylium ions from a linear precursor. Heating bis­(1-cyanovinyl acetate) in the presence of a trace amount of pyridinium p-toluenesulfonate results in a series of acyl group transfers and an intramolecular cyclization event to form a 3-oxidopyrylium ion that can be trapped by reaction with several dipolarophiles. When treated with dienes, the result is a sequential [5 + 2]/[4 + 2] cycloaddition reaction that provides sp3-rich products of high molecular complexity.

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