Journal of the American Chemical Society

Decarbonylation of tetrahydrofuran-2-carboxylic acids and tetrahydropyran-2-carboxylic acids in concentrated sulfuric acid: formation of oxonium ions

HA Bates

Index: Bates, Hans Aaron Journal of the American Chemical Society, 1982 , vol. 104, # 9 p. 2490 - 2493

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Citation Number: 13

Abstract

Abstract: Tetrahydrofuran-2-carboxylic acids 1, 3, and 5 readily decarbonylate in 96% sulfuric acid, generating stable oxonium ions 2, 4, and 6, respectively. Analogously, tetrahydropyran-2-carboxylic acids 7, 9, 12, and 14a produce oxonium ions 8, 10, 13, and 15, respectively. These oxonium ions are quite stable, with the exception of 10, which partially isomerizes to 11, and 13, which rearranges to ions 17 and 21. Details in the ...

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