Salts diphenyliodonium

I) The filtrate contains some diphenyliodonium salts these may be recovered as the sparingly soluble diphenyliodonium iodide (about 8 g.) (Section IV,27) by the addition of potassium iodide. 

Materials. The 1-propanol, glycerol and anthracene were obtained from Aldrich Chemical Company and were used as received. As in a previous study,17 a commercially available bis-(4-dodecylphenyl) iodonium hexafluoroantimonate salt (UV9310C GE Silicones) was used as the initiator. In this initiator, various dodecyl isomers have been attached to the phenyl rings of the diphenyliodonium salt to impart solubility in the monomer and do not effect the reactivity of the initiator.1 All studies were performed with an order of magnitude excess of initiator relative to anthracene. 

The general approach to 0-arylation of hydroxylamines involves N-protection followed by O-arylation. Activated aryl halides and heteroaryl halides easily alkylate oxime salts (equation 25), N-aUcyl hydroxamic acids and N-hydroxysuccinimide . N-Hydroxyph-thalimide can be also 0-phenylated through a reaction with diphenyliodonium salt, although in lower yield . ... 

A little diphenyliodonium salt may remain which will not dissolve. It will settle between the layers. 

A more efficient photoinitiator has been designed by combining the Eosin-MDEA system with diphenyliodonium salt. The quantum yield of photopolymerization of methyl methacrylate (7 M) in acetonitrile is 30 with MDEA (0.1 M) and diphenyliodonium (0.05 M). The molecular weight of the isolated polymer is 55,000. In the absence of quantum yield and molecular weight, respectively. Thus, the presence of diphenyliodonium decreases the quantum yield of initiation by approximately 40% and increases the value of k3/kt by a factor of 6. 

Electrochemical reduction of diphenyliodonium salts and phenylmercuric halides to benzene in DMF typically shows three or four waves depending on the concentration of supporting electrolyte or substrate, showing that the process involves reduction to iodobenzene, followed by further reduction to benzene21. 

RB2 has been replaced by the 9,10-dimethoxyanthracene-2-sulfonate and the products of the irradiation of the diphenyliodonium salt in degassed acetonitrile are the parent sulfonic acid, iodobenzene and benzene [226],... 

Table 7 give some data of the polymerization quantum yields (p) as a measure for the efficiency of various donor-diphenyliodonium salt combinations in the cationic polymerization of PGE. 

Fig. 3. Mechanism of Bronsted acid formation by photolysis of a diphenyliodonium salt (X BF4, SbF etc.)...

The crosslinking of such types of disiloxanes can be described by means of a cationic chain process. The diphenyliodonium salt 1 was used as initiator system for the monomers. 

MHz, below the 1897 MHz found in the free ligand, and q for iodine in the silver complex was quite substantial, 0.32. For diphenyliodonium salts values range from... 

Crafts-like reaction of this substance with benzene to form the diphenyliodonium salt (3) neutralization with ammonia then liberates the inner salt (4) which crystallizes from water as the monohydrate. 

The halogenonium series. r2Hal(X) and ArAr Hal(X) were synthesized and studied. They resembled iodonium salts very closely for example, the respective iodides, when treated with Mg or Sn (but not Tl, Pb, Bi) powders, produced the organometallics in a yield up to 60% 39), in analogy with the reaction reported by Sandin, McClure, and Irwin 29) for diphenyliodonium salts. 

Diphenyliodonium salts [IPh2]X E° — -0.9 V relative to FeCp2 [285]) are commercially available (X = Cl, Br, I) and the BF4, PFe, AsFe and SbFe can be made [286]. As aryldiazonium salts, they decompose, after electron transfer, to the phenyl radical which dimerizes to biphenyl and abstracts a H atom from the solvent. 

This synthesis of 1,2,3,4-tetraphenylnaphthalene (7) demonstrates the transient existence of benzyne (5), a hydrocarbon that has not been isolated as such. The precursor, diphenyliodonium-2-carboxylate (4), is heated in an inert solvent to a temperature at which it decomposes to benzyne, iodobenzene, and carbon dioxide in the presence of tetraphenylcyclo-pentadienone (6) as trapping agent. The preparation of the precursor (4) illustrates oxidation of a derivative of iodobenzene to an iodonium salt (2) and the Friedel-Crafts-like reaction of the substance with benzene to form the diphenyliodonium salt (3). Neutralization with ammoniuim hydroxide then liberates the precursor, inner salt (4), which, when obtained by crystallization from water, is the monohydrate. 

Zhang, M.-R., Kumata, K. and Suzuki, K. (2007)A Practical Route for Synthesizing a PET ligand containing [18F]fluorobenzene using reaction of diphenyliodonium salt with [18F]F. Tetrahedron Lett. 48, 8632-8635. 

---