Vicinal cis-dihydroxylation of alkenes has been carried out in good yields using tetradecyltrimethylammonium permanganate in a two phase solvent system with an inorganic base present from the beginning of the reaction. With benzyltrimethylammonium hydroxide as an organic base in nonaqueous solvent system reasonably good yields of diols are realised.
StewartR., Oxidation Mechanism, W.A. Benjamin, New York, N.Y., 1964, pp 58–76.
2.
(a) WibergK.B. and SaebarthK.A., J. Am. Chem. Soc., 1957, 79, 2822–2824
3.
LeeD.G. and BrownridgeJ.R., J. Am. Chem. Soc., 1973, 95, 3033–3034
4.
WibergK.B. and DeutschC.J., J. Am. Chem. Soc., 1973, 95, 3034–3035.
5.
FatiadiA.J., Synthesis1987, 85–127.
6.
FogliaT.A., BarrP.A. and MalloyA.J., J. Am. Oil. Chem. Soc., 1977, 54, 858A–861A.
7.
LeeD.G., In Phase Transfer Assisted Permanganate Oxidations: Oxidation in Organic Chemistry; Part D, TrahanovskyW. S., Eds. Academic Press, New York, 1982, pp 147–206.
8.
WeberW.P. and ShepherdJ.P., Tetrahedron Lett., 1972, 4907–4908.
9.
TaylorJ.E., WilliamsD., EdwardsK., OtonnaaD. and SamanichD., Can. J. Chem., 1984, 62, 11–15.
10.
OginoT. and MochizukiK., Chemistry Lett., 1979, 443–446.
11.
OginoT., Tetrahedron Lett., 1980, 177–180.
12.
BhushanV., RathoreR. and ChandrasekaranS., Synthesis, 1984, 431.
13.
HazraB.G., ChordiaM.D., BahuleB.B., PoreV.S. and BasuS., J. Chem. Soc., Perkin Trans. 1, 1994, 1667–1669.
14.
HazraB.G., ChordiaM.D., BasuS., BahuleB.B., PoreV.S. and NaskarD., J. Chem. Research, (S)1998, 8–9.
15.
ColemanJ.E., RicciutiC. and SwernD., J. Am. Chem. Soc., 1956, 78, 5342–5345.
16.
SharplessK. B. and AkashiK., J. Am. Chem. Soc., 1976, 98, 1986–1987.
