ARYLIODONIUM DERIVATIVES OF 2-AMINO-1,4-QUINONES - PREPARATION AND REACTIVITY

The reaction of 2-amino-1,4-quinones with [(hydroxy)(tosyloxy)iodo]are nes affords stable 2-amino-3-aryliodonio-1,4-quinones in high yields. The latter, upon treatment with alkali, are converted to the correspon ding zwitterionic 3-aryliodonio-1,4-quinone-2-imides. This new class o f compounds exhibits an interesting reactivity: upon heating, aryl mig ration from iodine to nitrogen is observed, while photochemical reacti on 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 intere sting multifunctional products. (C) 1997 Elsevier Science Ltd.