Organoiodine

In addition to its uses in photography and medicine, iodine and its compounds have been much exploited in volumetric analysis (iodometry and iodimetry, p. 864). Organoiodine compounds have also played a notable part in the development of synthetic organic chemistry, being the first compounds used in A. W. von Hofmann s alkylation of amines (1850), A. W. Williamson s synthesis of ethers (1851), A. Wurtz s coupling reactions (1855) and V. Grignard s reagents (1900). 

Leitner NKV (1998) Chlorination and formation of organoiodinated compounds the important role of ammonia. Environ Sci Technol 32 1680-1685. 

In recent years, a variety of hypervalent iodine reagents have been available. The versatility of these hypervalent organoiodine reagents in organic synthesis has been well recognized. Diaryliodonium salts constitute an important reagent class for the transfer of aryl groups. These iodonium ion salts have been used effectively in C-arylation of a variety of nucleopohiles.112 The arylation of the anion of nitroalkanes with diaryliodonium salts was already reported in 1963.113... 

As indicated, only elemental iodine is found in the combustion products of organoiodine compounds [61,62,67]. The iodine formed in a static bomb is mostly in the crystalline state, but some is present in the aqueous and in the gaseous phases. The thermal corrections for dissolution and sublimation are very small and, therefore, static-bomb calorimeters may be used to study organoiodine compounds. However, to avoid the uncertainty in the final state due to the distribution... 

Schall, C., and K. G. Heumann, GC Determination of Volatile Organoiodine and Organobromine Compounds in Arctic Seawater and Air Samples, Fresenius J. Anal. Chem., 346, 717-722... 

Organoiodine compounds are somewhat unusual in that their absorption cross sections are sufficiently red-shifted that they absorb in the actinic region (A > 290 nm) and hence photolyze in the troposphere. Use the data for Cl I, I in Table 4.42, Chapter 4, to estimate the lifetime of this compound with respect to photolysis at the earth s surface at a solar zenith angle of 50° on May 1. How does this compare to its lifetime with respect to reaction with OH at 1 X 106 radicals cm 3 if the rate constant is 7.2 X 10 14 cm3 molecule 1 s 1 ... 

Keppler F, Biester H, Putschew A, Silk PJ, Schdler F1F, Muller G (2004) Organoiodine Formation during Humification in Peatlands. Environ Chem Lett 1 219... 

Schall C, Heumann KG, Kirst GO (1997) Biogenic Volatile Organoiodine and Organo-bromine Hydrocarbons in the Atlantic Ocean from 42°N to 72°S. Fresenius J Anal Chem 359 298... 

Schall C, Latumus F, Heumann KG (1994) Biogenic Volatile Organoiodine and Organo-bromine Compounds Released from Polar Macroalgae. Chemosphere 28 1315... 

Latumus F, Giese B, Wiencke C, Adams FC (2000) Low-Molecular-Weight Organoiodine and Organobromine Compounds Released by Polar Macroalgae - The Influence of Abiotic Factors. Fresenius J Anal Chem 368 297... 

M. Ochiai, Y. Nagao Hypervalent organoiodine compounds in organic synthesis reaction with organosilicon and tin [12]... 

D. Wang Application of hypervalent organoiodine compounds in synthesis [17]... 

The formation of carbon-heteroatom bonds can be effected by reactions of hypervalent iodine reagents with a wide range of organic substrates and inorganic nucleophiles, and represents one of the most popular applications of organoiodine(III) compounds [1-10]. Except for C-I(III) bond forming reactions used for the synthesis of iodanes and iodonium salts, C-heteroatom bond formation is almost always accompanied by reduction of the hypervalent iodine reagents to iodine(I) compounds. 

Dohi T, Ito M, Morimoto K, Wata M, Kita Y (2008) Oxidative cross-coupling of arenes induced by single-electron transfer leading to biaryls by use of organoiodine(III) oxidants. Angew Chem Int Ed 47 1301-1304... 

The Synthesis of Heterocyclic Compounds with Hypervalent Organoiodine Reagents... 

Except for the Dess-Martin periodane, which has been widely employed as a selective oxidant in various synthetic protocols (97MI1, 02CRY2523), organoiodine(Y) compounds have received much less attention than their iodine(III) counterparts for organic synthesis. However, recent publications in this area indicate that this is likely to change. 

Applications to the synthesis of heterocyclic compounds of hypervalent organoiodine reagents are covered by Gerald Koser (University of Akron, Ohio) who is well known for his own book in the field. The present review provides continuity with the earlier comprehensive treatment of the subject by Moriarty and Prakmash in Volume 69 of Advances in Heterocyclic Chemistry, which covered the field up through 1996. 

With respect to iodine chemistry, the major sources of iodine are thought to be from macroalgal sources releasing organoiodine com-... 

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