Green Oxidations
651
Experimental
References
The oxidant for the reactions reported in the first column of
Table 1 was prepared by grinding together potassium perman-
ganate (1.0 g) and MnSO ꢁ H O (1.0g). This oxidant was
[1] Singh N, Lee DG (2000) Org Process Res Dev 5: 599
[2] Shaabani A, Mirzaei P, Lee DG (2004) Catal Lett 97:
119
[3] Toda F, Takum H, Yamaguchi H (1989) Chem Exp 4:
507
[4] Tanaka K, Kishigami S, Toda F (1991) J Org Chem 54:
4333
[5] Toda F, Tanaka K, Hamai K (1999) J Chem Soc Perkin
Trans 1: 3307
[6] Toda F, Takumi H, Akehi M (1990) Chem Commun 1270
[7] a) Rao PS, Venkataratnam RV (1991) Tetrahedron Lett
32: 5821; b) Sugino T, Tanaka K (2001) Chem Lett 110;
c) Bose DS, Narsaiah AV (2001) J Chem Research (S)
36; d) Sabitha G, Reddy BVS, Satheesh RS, Yadav JS
(1998) Chem Lett 773; e) Bogdal D (1998) J Chem
Research (S) 468; f) Balalaie S, Nemati N (2000) Synth
Commun 30: 869
[8] a) Ballini R, Marziali P, Mozzicafreddo A (1996) J Org
Chem 61: 3209; b) Christoffers J (1997) J Chem Soc
Perkin Trans 1: 3141; c) Diez-Barra E, dela Hoz A,
Merino S, Rodriguez A, Sanchez-Verdu P (1998) Tetra-
hedron 54: 1835; d) Kotsuki H, Arimura K, Ohishi T,
Maruzasa R (1999) J Org Chem 64: 3770; e) Loupy A,
Sansoulet J, Zaparucha A, Merienne C (1998) Tetrahe-
dron Lett 30: 333; f) Michaud D, Boullet FT, Hamelin J
(1997) Tetrahedron Lett 38: 7563; g) Ranu BC, Saha M,
Bhar S (1997) Synth Commun 27: 621
4
2
placed in a round bottom flask (in the absence of solvent)
and reductant (1.0mmol) was added. The reactants were stir-
red continuously at room temperature using a magnetically
controlled stirring bar. Progress of the reactions was monitored
by TLC until the reductant had completely reacted or until a
reasonable amount of time had elapsed. Methylene chloride
3
15 cm ) was then added to the flask and the reaction mixture
(
was filtered through a sintered glass funnel. The residue was
3
washed with additional methylene chloride (2ꢂ10 cm ) and
the solvent collected was combined and evaporated on a flash
evaporator. The yields were determined by GC analysis or
1
from the integrals of the H NMR spectrum of the material
obtained when most of the solvent had been evaporated. All
1
products are known compounds with well-defined H NMR
spectra [11].
The results reported in the second column of Table 1 were
obtained in the same way except that the oxidant consisted of
KMnO (1.0g) and MnSO ꢁ H O (0.20 g).
4
4
2
The results reported in the third column of Table 1 were
obtained using heterogeneous conditions. KMnO (1.0g) and
4
MnSO ꢁ H O (1.0g) were ground together and placed in a
4
2
3
round bottom flask, followed by methylene chloride (15 cm )
and reductant (1.00 mmol). The reaction was then monitored
and worked up as described above.
[9] Shaabani A, Lee DG (2001) Tetrahedron Lett 42: 5833
10] a) Regen SL, Koteel C (1977) J Am Chem Soc 99: 3837;
b) Lai S, Lee DG (2001) Synthesis 1645
[11] Shaabani A, Mirzaei P, Naderi S, Lee DG (2004)
Tetrahedron 60: 11415
[
Acknowledgements
Financial assistance from the Research Council of Shahid
Beheshti University of Iran is gratefully acknowledged.