Abstract
Benzene, halobenzenes, and a number of more or less deactivated arenes, including nitrobenzene, readily reacted in anhydrous HIO3/AcOH/Ac2O/conc. H2SO4 mixtures to probably give ArIO2 intermediates or other hypervalent species (not isolated). The final reaction mixtures were poured into excess aq. Na2SO3 solution (a reductant) to give the purified iodinated products in 39-83% yields.
Highlights
In 1892 Meyer and Wachter [1], in describing iodosylbenzoic acid, the first iodosylarene, included there the following passage: “Ferner ist zu prüfen, ob man durch Behandlung von aromatischen Substanzen mir Schwefelsäure und Jodsaüre, - JO2OH, entsprechend der Reaction der Salpetersäure, NO2OH, - Verbindungen mit der Gruppe -JO2 erhalten kann
In 1935 Masson and co-workers [2] had established that benzene derivatives and HIO3 in sulfuric acid readily formed diaryliodonium salts in high yield; later on, their initial discovery was extended considerably [3]: I+3 + 2 ArH
Some experimental evidence was given that a primary deoxidation of the iodic acid to the iodous stage by a fraction of the aromatic reagent, ArH, was followed by the direct interaction of the iodous acid and the aromatic reagent to give the diaryliodonium salts; aryl iodides were formed there as side products, and the production of CO2 was observed
Summary
In 1892 Meyer and Wachter [1], in describing iodosylbenzoic acid, the first iodosylarene, included there the following passage: “Ferner ist zu prüfen, ob man durch Behandlung von aromatischen Substanzen mir Schwefelsäure und Jodsaüre, - JO2OH, entsprechend der Reaction der Salpetersäure, NO2OH, - Verbindungen mit der Gruppe -JO2 erhalten kann. Rudzki [8] on reacting chlorobenzene with HIO3 in anhydrous Ac2O/concd H2SO4 mixtures, under widely varied reaction conditions, obtained in the best possible manner 4-chloroiodylbenzene, 4-ClC6H4IO2, albeit in only 18% crude yield. We have established [9] that benzene, halobenzenes and some deactivated arenes (excluding nitrobenzene) readily reacted in anhydrous NaIO4/AcOH/Ac2O/concd H2SO4 mixtures.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
