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1-Hydroxypyrroles, 1-hydroxyindoles And 9-hydroxycarbazoles

R. Acheson
Published 1990 · Chemistry

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Publisher Summary This chapter focuses on 1-hydroxypyrroles, 1-hydroxyindoles, and 9-hydroxycarbazoles. 1-Hydroxypyrrole is a colorless liquid, which has not been analyzed, and which decomposed on attempted distillation under high vacuum. 1-Hydroxyindole is a reactive compound that has only been obtained in solution; it polymerizes to a green powder on attempted isolation. Its 4-benzyloxy derivative also could not be isolated and these compounds are more difficult to handle than 1-hydroxypyrrole. Reduction of a 1-hydroxyindole to the corresponding indole is always effected by zinc and acetic acid if sufficiently vigorous conditions are employed by other reagents, including trimethyl phosphate titanium(III) chloride under the correct conditions and by Raney nickel/sodium hypophosphite. The instability of 1-hydroxyindole itself may well be due, in part, to radical formation and polymerization. N- Hydroxycarbazole was first postulated as an intermediate in the reaction of benzyne with nitrosobenzene, which gave N-phenylcarbazole. Carbazole can be oxidized to the 9-oxyl radical, which has been identified in fish liver; it may be related to tumor production. A small number of 9-hydroxycarbazoles has been made.
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