Abstract
Benzene, halobenzenes and some deactivated arenes readily reacted in anhydrous NaIO4/AcOH/Ac2O/concd. H2SO4 mixtures to afford, after quenching with excess aqueous Na2SO3 solution (a reducing agent), purified iodinated products in 27-88% yields. This novel method of aromatic iodination is simple, fairly effective and environmentally safe.
Highlights
Inorganic iodine(VII) derivatives are known and up to now not a single organoiodine(VII) compound has been synthesized and investigated [1,2]
Mattern [5] improved the above protocol for preparing either C6I6 (45%) or 1,2,4,5-C6H2I4 (60%) from benzene, but he made no attempt to study the green and red intermediates observed by Levitt and Iglesias [4]
As a continuation of our systematic studies on effective aromatic iodination reactions, which are related in detail in our two latest reviews [7,8], we recently decided to use sodium periodate NaIO4, alone, as an iodinating reagent
Summary
Inorganic iodine(VII) derivatives are known and up to now not a single organoiodine(VII) compound has been synthesized and investigated [1,2]. Lewitt and Iglesias [4] attempted to prepare PhIO3 by adding benzene dropwise to a chilled solution of H5IO6 in concd. H2SO4 solution, after adding the benzene, turned first green, red, and light yellow, as the yellowtan C6I6 gradually precipitated out.
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