The Michael adduct of L-ascorbic acid to methyl vinyl ketone: its remarkable self-condensation and other reactions
R Arnold, G Fodor, C George…
Index: Arnold, Regina; Fodor, Gabor; George, Clifford; Karle, Isabella Canadian Journal of Chemistry, 1987 , vol. 65, p. 131 - 136
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Citation Number: 8
Abstract
The structure of the Michael adduct of l-ascorbic acid (1) to methyl vinyl ketone was established as 2-(3-oxobutyl)-3-oxo-l-gulonolactone hemiketal (3). In aqueous solution 3 is prone to undergo base-or acid-promoted degradations. 1-(2-Furyl)-1, 4-pentanedione was isolated from the acidic product mixture. Under strictly anhydrous acid-catalyzed conditions, if a suitable nucleophile like ethanol is present, the tricyclic ethyl ketal 6 b forms. In the ...
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