1,3-Dipolar character of six-membered aromatic rings. Part 51. Cycloadditions of 1-(β-benzoylvinyl)-3-oxidopyridiniums and subsequent transformations
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 362-371
- https://doi.org/10.1039/p19800000362
Abstract
β-p-Chloro-, β-p-bromo-, and β-2-chloro-5-nitrobenzoyl-vinyl chloride react with 3-hydroxypyridine to give quaternary salts which with base give the corresponding betaines. These betaines undergo thermal dimerisation and cycloadditions with mono- and di-enes at the 2,6- and 2,4-positions, respectively. The site-, regio-, and stereo-selectivity of these cycloadditions are discussed with reference to MO predictions. The β-aroylvinyl substituents in the adducts can be hydrolytically removed.Keywords
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