571166-63-7Relevant articles and documents
Studies on the reactivity of aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone: Reactions with amines
Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros,Tsanakopoulou, Maria
, p. 5627 - 5631 (2007/10/03)
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.