Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes

Barton OG, Mattay J (2008)
Synthesis 2008(1): 110-114.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
A simple method for the iodination of activated arenes, using molecular iodine and sodium peroxodisulfate as the oxidant, is presented. The reaction is conducted in the presence of catalytic amounts of tetramethylammonium iodide as a phase-transfer cata- lyst in acetonitrile. For non-polar substances, which are not soluble in pure acetonitrile such as calix[4]arenes bearing long alkyl chains, a modified reaction is introduced. In this case the phase-transfer catalyst is changed to methyltriphenylphosphonium peroxodisulfate. Chloroform as a cosolvent mediates solubility. Furthermore, we show that the slightly basic conditions obtained upon the addition of sodium bicarbonate have a beneficial effect on the yield.
Erscheinungsjahr
Zeitschriftentitel
Synthesis
Band
2008
Zeitschriftennummer
1
Seite
110-114
ISSN
eISSN
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Barton OG, Mattay J. Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes. Synthesis. 2008;2008(1):110-114.
Barton, O. G., & Mattay, J. (2008). Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes. Synthesis, 2008(1), 110-114. doi:10.1055/s-2007-1000826
Barton, O. G., and Mattay, J. (2008). Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes. Synthesis 2008, 110-114.
Barton, O.G., & Mattay, J., 2008. Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes. Synthesis, 2008(1), p 110-114.
O.G. Barton and J. Mattay, “Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes”, Synthesis, vol. 2008, 2008, pp. 110-114.
Barton, O.G., Mattay, J.: Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes. Synthesis. 2008, 110-114 (2008).
Barton, Olaf G., and Mattay, Jochen. “Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes”. Synthesis 2008.1 (2008): 110-114.