Studies on the Reactivity of Aryliodonium Ylides of 2-Hydroxy-1,4-naphthoquinone:  Reactions with Amines

Aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone react with amines in refluxing dichloromethane to afford good yields of indanedione 2-carboxamides 5, through a ring-contraction and α,α ‘ -dioxoketene formation reaction. These amides exist in solution in an unusual enol−amide form. In contrast, t...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-07, Vol.68 (14), p.5627-5631
Main Authors: Malamidou-Xenikaki, Elizabeth, Spyroudis, Spyros, Tsanakopoulou, Maria
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary:Aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone react with amines in refluxing dichloromethane to afford good yields of indanedione 2-carboxamides 5, through a ring-contraction and α,α ‘ -dioxoketene formation reaction. These amides exist in solution in an unusual enol−amide form. In contrast, the same reactants in a copper-catalyzed reaction afford arylamines and 3-iodo-4-hydroxy-1,2-naphthoquinone.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0343679