The highly regioselective cleavage of epoxides by means of molecular iodine and bromine in the presence of metalloporphyrins affords vicinal iodohydrins and bromohydrins in high yields.
References
1.
BoniniC. and RighiG., Synthesis, 1994, 225;
2.
IranpoorN. and BaltorkI. Mohammad-pour, Synth. Commun., 1990, 20, 2789;
3.
SmithJ. G., Synthesis, 1984, 629.
4.
Fieser and Fieser, Reagent for organic synthesis, ed. SmithJ. G. and FieserM., John Wiley, New York, 1990, looking for: Halohydrins and Derivatives.
5.
ChiniM., CrottiP., GardelliC. and MacchiaF., Tetrahedron, 1992, 48, 3805.
6.
KonaklievaM. I., DahiM. L. and TurosE., Tetrahedron Lett., 1992, 33, 7093.
7.
KurodaY., SuzukiY. and OgoshiH., Tetrahedron Lett., 1994, 35, 749 and references cited therein.
8.
MohajerD. and TangestaninejadS., J. Chem. Soc., Chem. Commun., 1993, 240 and references cited therein;
9.
FirouzabadiH., SardarianA. R., KhayatZ., KarimiB., and TangestaninejadS., Synth. Commun., 1997, 27, 2709.
10.
BartoliJ. F., BattioniP., De FoorW. R. and MansuyD., J. Chem. Soc., Chem. Commun., 1994, 23.
11.
FirouzabadiH., KhayatZ., SardarianA. R. and TangestaninejadS., Iran. J. Chem. Chem. Eng., 1996, 15, 54.
12.
SuhY. G., KooB. A., KoJ. A. and ChoY. S., Chem. Lett., 1993, 1907.
13.
NourE. M. and ShahadaL. A., Spectrochicn. Acta. Part A, 1988, 44, 1277;
14.
NourE. M., Spectrochim. Acta, Part A, 1991, 47, 473.
15.
SemnaniA. and ShamsipurM., J. Chem. Soc., Dalton Trans., 1996, 2215.
16.
HopkinsH. P., JahagirdarD. V. and WindierF., J. Phys Chem., 1978, 82, 1254.
17.
LangR. P., J. Phys. Chem., 1974, 78, 1657;
18.
AndrewsL. J., ProchaskaE. S. and LoewenschussA., Inorg. Chem., 1980, 19, 463.
19.
MizunoM., TanakaJ. and HaradaI., J. Phys. Chem., 1981, 85, 1789.
20.
WinsteinS. and HendersonR. D., J. Am. Chem. Soc., 1943, 65, 2190.
21.
OlahG. A., FungA. P. and MeiderD., Synthesis, 1981, 280.
22.
PosnerG. H., RogersD. Z., KinzigC. H. and GurriaG. M., Tetrahedron Lett., 1975, 42, 3597.
