8
74
B. S. Chhikara et al.
LETTER
Another advantage of tert-butanol is that it has a better
range of solubility for organic compounds than hydro-
carbons, which were used earlier as solvents. Hence
the use of tert-butanol in our system makes the reaction
easier and faster giving 100% conversion of alcohols into
ketones within one hour as compared to the earlier reports
where these reactions were taking place in 4–8 hours.
(2) For an overview of alcohol oxidation catalysis, see:
a) Muzart, J. Chem. Rev. 1992, 92, 113. (b) Seddon, K. R.;
(
Stark, A. Green Chem. 2002, 4, 119. (c) Shaabani, A.;
Mirzaei, P.; Lee, D. G. Catal. Lett. 2004, 97, 119.
(
d) Chhikara, B. S.; Chandra, R.; Tandon, V. Tetrahedron
Lett. 2004, 45, 7585. (e) Wan, Q. Synlett 2004, 1847.
f) Adak, A. K. Synlett 2004, 1651. (g) Oba, M.; Endo, M.;
Nishiyama, K.; Ouchi, A.; Ando, W. Chem. Commun. 2004,
0, 1672. (h) Moorthy, J. N.; Singhal, N.; Venkatakrishnan,
(
1
In conclusion, we describe herein an efficient protocol for
oxidation of primary and secondary alcohols with hydro-
gen peroxide in quasi-homogenous system. This protocol
is high yielding, clean, safe, operationally simple and cost
effective.
P. Tetrahedron Lett. 2004, 45, 5419. (i) Lee, J. C.; Lee, J.
Y.; Lee, S. J. Tetrahedron Lett. 2004, 45, 4939. (j) Guo,
M.-L. Green Chem. 2004, 6, 271. (k) Reddy, S. R.; Das, S.;
Punniyamurthy, T. Tetrahedron Lett. 2004, 45, 3561.
(l) Bressette, A. R.; Glover, L. C. I. V. Synlett 2004, 738.
(
(
m) Chhikara, B. S.; Tehlan, S.; Kumar, A. Synlett 2005, 63.
n) Pillai, U. R.; Sahle-Demessie, E. Green Chem. 2004, 6,
1
61. (o) Velusamy, S.; Punniyamurthy, T. Org. Lett. 2004,
Representative Procedure
Diphenylmethanol (1.84 g, 10 mmol), sodium tungstate (164 mg,
6, 217. (p) Tehlan, S.; Hundal, M. S.; Mathur, P. Inorg.
Chem. 2004, 43, 6589.
0
.5 mmol) and tetrabutyl ammonium hydrogen sulfate (169 mg, 0.5
mmol) were taken in t-BuOH (2 mL). The reaction mixture was
heated to 90 °C and H O added (30% soln, 1.72 mL, 15 mmol)
(
3) (a) Jones, C. W. Application of Hydrogen Peroxide and
Derivatives; MPG Books Ltd.: Cornwall UK, 1999.
(b) Jorgensen, K. A. Chem. Rev. 1989, 89, 431. (c) Jones,
C. W. Application of Hydrogen Peroxide and Derivatives;
Royal Society of Chemistry: Cambridge, 1999.
2
2
drop-wise with rapid stirring. On complete addition of H O , small
aliquots (10 mL) of reaction mixture were taken at different time in-
tervals and monitored by gas chromatography.
2
2
(
d) Catalytic Oxidations with Hydrogen Peroxide as
Oxidant; Strukul, G., Ed.; Kluwer Academic: Dordrecht The
Netherlands, 1992.
Acknowledgment
(
4) For selected peroxometalate-catalyzed oxidation examples,
see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org.
Chem. 1963, 28, 1140. (b) Ishi, Y.; Tanaka, H.; Nisiyama,
Y. Chem. Lett. 1994, 1. (c) Stec, Z.; Zawadiac, J.; Skibinski,
A. C.; Nogueira, H. I. S.; Parkin, B. C. J. Mol. Catal. 1997,
The authors are grateful to Professor Sukh Dev, FNA, for his in-
valuable suggestions and constant support provided for this work.
BSC thanks Council for Scientific and Industrial Research (CSIR)
for providing research grant.
117, 185. (d) Ventrurello, C.; Gambaro, M. J. Org. Chem.
1991, 56, 5924. (e) Arends, I. W. C. E.; Sheldon, R. A.;
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Synlett 2005, No. 5, 872–874 © Thieme Stuttgart · New York