title: Bis(1-cyanovinyl acetate) Is a Linear Precursor to 3-Oxidopyrylium Ions.
abstract: 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.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Sidney Malik
authors.initials: SM
authors.lastname: Wilkerson-Hill
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Shota
authors.initials: S
authors.lastname: Sawano
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Richmond
authors.initials: R
authors.lastname: Sarpong
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D007477:Ions; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: C559665:1-cyanovinyl acetate; D006575:Heterocyclic Compounds, 3-Ring; D007477:Ions; D011726:Pyridinium Compounds; D014753:Vinyl Compounds