18543-92-5Relevant articles and documents
Aromatic Iodination: Evidence of Reaction Intermediate and of the ?-Complex Character of the Transition State
Galli, Carlo
, p. 3238 - 3245 (1991)
The reactivity of the four different procedures of aromatic iodination is compared under the same experimental conditions, and their selectivity toward two substrates in competition, i. e., mesitylene (1,3,5-trimethylbenzene, MES) and durene (1,2,4,5-tetramethylbenzene, DUR), is evaluated.Two of these procedures, namely, S2O82-/I2 and Ce(IV)/I2, present strong oxidizing capacity.Since the same MES/DUR relative reactivity is obtained from the four procedures, it becomes possible to state that a common reactive intermediate, most likely the I+ ion, is generated.The use of the MES/DUR mechanistic probe allows one to describe the reactivity picture of the iodination reaction as one of electrophilic substitution at the aromatic nucleous, with a transition state properly represented in terms of a ?-complex.The radical cation of durene also forms when the iodination is carried out by means of oxidizing agents, but it is solely responsible for the formation of side-chain substitution products and is not involved in the nuclear substitution process.
Decomposition of Benzoyl Peroxide in the Presence of Alkylaromatic Compounds. A Facile Side-Chain Substitution Reaction
Wistrand, Lars-Goeran
, p. 812 - 814 (2007/10/02)
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