Activated aromatics are effectively converted, at room temperature and within 15min, into the corresponding mono-, di- or tri-iodinated products in anhydrous l2-Phl(OAc)2-AcOH-Ac2O systems, acidified with catalytic amounts of conc. H2SO4.
References
1.
MarchJ., Advanced Organic Chemistry, Reactions, Mechanisms, and Structures, Wiley, New York, 1992, 4th edn., pp. 531–534 and references therein.
2.
PriceD., IddonB., and WakefieldB. J., Bromine Compounds. Chemistry and Applications, Elsevier, Amsterdam, 1988.
3.
MerkushevE. B., Advances in the Synthesis of Iodoaromatic Compounds, Synthesis, 1988, p. 923.
4.
VarvoglisA., The Organic Chemistry of Polycoordinated Iodine, VCH, New York, 1992.
5.
VarvoglisA., Hypervalent Iodine in Organic Synthesis, Academic, San Diego, 1997.
6.
MurakiT., TogoH., and YokoyamaM., Synlett, 1998, 286.
7.
TogoH., NogamiG., and YokoyamaM., Synlett, 1998, 534.
8.
OgataY., and AokiK., J. Am. Chem. Soc., 1968, 90, 6187.
9.
Aldrich Catalogue Handbuch of Fine Chemicals 1999–2000: (a) 222.50 DM/100g of 2; (b) 325.90 DM/2 × 50g of 5; (c) 780.00 DM/4 × 25g of 6. See useful information submitted therein.
10.
Krassowska-ŚwiebockaB., LulińskiP., and SkulskiL., Synthesis.1995, 926.
11.
LulińskiP., and SkulskiL., Bull. Chem. Soc. Jpn., 1997, 70, 1665.
12.
LulińskiP., and SkulskiL., Bull. Chem. Soc. Jpn., 1999, 72, 115, see also ref. 1 therein.
13.
KaźmierczakP., and SkulskiL., Synthesis, 1998, 1721.
