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The reaction of 2-amino-1,4-quinones with [(hydroxy)(tosyloxy)iodo]arenes affords stable 2-amino-3-aryliodonio-1,4-quinones in high yields. The latter, upon treatment with alkali, are converted to the corresponding zwitterionic 3-aryliodonio-1,4-quinone-2-imides. This new class of compounds exhibits an interesting reactivity: upon heating, aryl migration from iodine to nitrogen is observed, while photochemical reaction with aromatic compounds and 2,3-dihydrofuran leads to substitution products. Nucleophilic attack of sodium alkoxides on these zwitterions results in opening of the quinone ring affording synthetically interesting multifunctional products. © 1997 Elsevier Science Ltd. |
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