131. The kinetics of the decomposition of diphenyliodonium iodide

Redox Initiated Cationic Polymerization: Reduction of Triarylsulfonium Salts by Silanes

“…Although diaryliodonium and triarylsulfonium salts behave similarly with respect to their photochemical properties, their thermo-and radiochemistries are quite different. Due to the low bond energy of the C-I bond (22 kcal/mol) [7] in diaryliodonium salts, these compounds function well as thermal cationic initiators at temperatures above 120°C. In contrast, the greater stability of triarylsulfonium salts makes them impractical for use as thermal cationic initiators.…”

An Alternative to the Sandmeyer Approach to Aryl Iodides

“…Moreover,i th as been known for more than ac entury that diaryliodonium compounds [38][39][40] can be converted to aryl iodides efficiently using iodide salts under mild conditions. [41,42] Here we show that an operationally simple, two-step approach, which involves formation of areadily purified diaryliodoniums alt intermediate and conversion of this intermediate to an iodoarene, is an effective and general process for the selective synthesis of al arge varietyo fm onoiodinated arenes.M ost surprising is that this process occurs with greater reactivity and selectivity than those employing most common electrophiliciodination reagents.The two-step iodination process is outlined in Scheme 2. The optimization of reaction conditions using aryliodination reagents 1-(diacetoxyiodo)-4-nitrobenzene 1a,a nd dimethyl 5-(diacetoxyiodo)isophthalate 1b is summarized in Ta ble 1.…”

Organic Compounds of Polyvalent Iodine.

“…Fletcher and Hinshelwood (16) have studied the rate of decomposition of diphenyliodonium iodide in the solid state and in solution in iodobenzene. The activation energy for the reaction in the solid state was found to be 26,300 calories and that for the reaction in solution was 27,000 calories (uncorrected for change in viscosity).…”