Bis(1-cyanovinyl acetate) Is a Linear Precursor to 3-Oxidopyrylium Ions
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.
Photosolvolysis of bridgehead quaternary ammonium salts. II. Synthesis of some 2,5-benzoxazonine derivatives and attempted synthesis of the 1,2,4,5,6,7-hexahydro-3,5-benzoxazonine system
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Bremner,Winzenberg
p. 1659 - 1676
(2007/10/02)
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