Microwave-Accelerated or Conventionally Heated Iodination Reactions of Some Aromatic Amines, Using ortho-Periodic Acid as the Oxidant †
Results and Discussion
- by conventional heating: the vigorously stirred reaction mixtures were gently boiled under a reflux condenser for 10-210 minutes (see Table 1);
- by focused monomode microwave irradiation, under an externally attached reflux condenser and with stirring: the reaction mixtures were placed into the microwave cavity and were then irradiated for 2-20 minutes (Table 1); an appropriate power output was used to secure a mild, uninterrupted reflux of the solvent.
|Iodinated product||M.p. (˚C)||Lit.  m.p. (˚C)||Conventional method||MW method|
|time [min]||yield [%]||time [min]||yield [%]|
|4-I-C6H4NHEt||53.5-54.3||not found b)||60||66||10||61|
- Satisfactory microanalyses obtained for the purified products: I ±0.3%.
- Probably a new compound. Calcd. for C8H10IN: C, 39.02; H, 4.07; I, 50.96%; Found: C, 39.0; H, 4.2; I, 50.9%.
- Admixed with ca. 10% of its ortho isomer (as established from its 1H- and 13C-NMR spectra).
Microwave-Accelerated Iodination Reactions
References and Notes
- a) Microwave-Enhanced Chemistry Fundamentals, Sample Preparation and Applications; Kingston, H. M.; Haswell, S. J. (Eds.) American Chemical Society: Washington, D. C., 1997. b) Microwaves in Organic Synthesis; Loupy, A. (Ed.) Wiley-VCH: Weinheim, 2002. c) Microwave Synthesis; Chemistry at the Speed of Light; Hayes, B. L. (Ed.) CEM Publishing: Matthews, NC, 2002.
- Perreux, L.; Loupy, A. A tentative realization of microwave effects in organic synthesis according to the reaction medium, and mechanistic consideration. Tetrahedron 2001, 57, 9199–9223, A review. [Google Scholar]
- Lindstroem, P.; Tierney, J.; Whathey, B.; Westman, J. Microwave assisted organic synthesis – a review. Tetrahedron 2001, 57, 9225–9283. [Google Scholar]
- For a review see: Fini, A.; Breccia, A. Chemistry by Microwaves. Pure Appl. Chem. 1999, 71, 573–579. [Google Scholar]
- Lulinski, P.; Kryska, A.; Sosnowski, M.; Skulski, L. Eco-friendly Oxidative Iodination of Various Arenes with a Urea-Hydrogen Peroxide Adduct (UHP) as the Oxidant. Synthesis 2004, 441–445. [Google Scholar]
- Sosnowski, M.; Skulski, L. Microwave-Accelerated Iodination of Some Aromatic Amines, Using Urea-Hydrogen Peroxide Addition Compound (UHP) as the Oxidant. Molecules 2002, 7, 867–880, Avail. at URL: http://www.mdpi.org/molecules/papers/71200867.pdf. [Google Scholar]
- Dictionary of Organic Compounds, 6th ed.; Chapman & Hall: London, 1996.
- Sample Availability: Available from the authors.
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Sosnowski, M.; Skulski, L.; Wolowik, K. Microwave-Accelerated or Conventionally Heated Iodination Reactions of Some Aromatic Amines, Using ortho-Periodic Acid as the Oxidant †. Molecules 2004, 9, 617-621. https://doi.org/10.3390/90700617
Sosnowski M, Skulski L, Wolowik K. Microwave-Accelerated or Conventionally Heated Iodination Reactions of Some Aromatic Amines, Using ortho-Periodic Acid as the Oxidant †. Molecules. 2004; 9(7):617-621. https://doi.org/10.3390/90700617Chicago/Turabian Style
Sosnowski, Maciej, Lech Skulski, and Katarzyna Wolowik. 2004. "Microwave-Accelerated or Conventionally Heated Iodination Reactions of Some Aromatic Amines, Using ortho-Periodic Acid as the Oxidant †" Molecules 9, no. 7: 617-621. https://doi.org/10.3390/90700617