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Trends in Heterocyclic Chemistry   Volumes    Volume 10 
Abstract
Correction of the literature citing monoiodo-8-quinolinols: a critical review
Donald D. Clarke, Herman Gershon
Pages: 67 - 72
Number of pages: 6
Trends in Heterocyclic Chemistry
Volume 10 

Copyright © 2005 Research Trends. All rights reserved

ABSTRACT

Until 1995, all papers that claimed preparation or further study with monoiodo-8-quinolinol were really working with the 7-iodo isomer. Of the 83 relevant citations 67 dealt with incorrect structural assignments, 13 were critiqued due to errors made in synthesis and interpretation, and 9 had the correct structural assignments. This literature review made the following conclusions apparent. 1. Prototropic forms of 8-quinolinol influence orientation of electrophiles. 2. Under strong acidic conditions, the 5 position is favored. 3. Under mild acidic conditions, mixtures of 5 and 7 substituted compounds are formed. 4. Under basic conditions, the incoming electrophile favors the 7 position. 5. When the phenolic group is etherified or complexed with metals, only 5 substitution takes place, and 7 substitution occurs only after the 5 position is filled. 6. NXS is generally a superior halogenating agent than elemental halogen. 7. In order to avoid rearrangements, the more electronegative group should be put into the desired position followed by the less electronegative substituent.

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