J. CHEM. RESEARCH (S), 1999 561
tetramethylsilane as the internal standard. Montmorillonite KSF was
purchased from Aldrich. The reactions were carried out in a domestic
microwave oven (BPL-SANYO, BMO-700T, 1200 W).
3
4
5
M. D. So¡er, M. P. Bellis, H. E. Gellerson and R. A. Stewart,
Org. Synth., Coll. Vol. 4, John Wiley & Sons, New York, 1992,
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A. McKillop and D. W. Young, Synthesis, 1979, 481; J. M.
Riego, Z. Sedin, J. M. Zaldivar, N. C. Marziazo and C.
Tortalo, Tetrahedron Lett., 1996, 37, 513.
General Procedure.öA mixture of bisul¢te addition product
(
1 mmol) and montmorillonite KSF (300 mg) was taken in a 25 ml
Erlenmeyer £ask and kept over an alumina bath (heat sink) inside
a domestic microwave oven and irradiated for 5^20 s and the reaction
was monitored by TLC. The product was extracted with ethyl acetate
S. Caddick, Tetrahedron, 1995, 51, 10403; S. A. Galema,
Chem. Soc. Rev., 1997, 26, 233; F. Langa, P. D. L. Cruz,
A. D. L. Hoz, A. Diaz-Ortiz and E. Diez-Barra, Contemp. Org.
Synth., 1997, 4, 373; A. K. Bose, B. K. Banik, N. Lavlinskaia,
M. Jayaraman and M. S. Manhas, CHEMTECH, 1997, 27, 18;
A. K. Mitra, A. De and N. Karchaudhuri, Synth Commun.,
1999, in press.
(
2 Â 5 ml), washed with brine and dried over anhydrous sodium
sulfate. Evaporation of the solvent a¡orded the products in excellent
yield (Table 1). All the products were characterised by 1H NMR
spectroscopy and by comparison with IR spectra of authentic
samples.
6
V. K. Ahluwalia, B. Goyal and U. Das, J. Chem. Res (S),
1
997, 266; H. M. Sampath Kumar, P. K. Mohanty, M. Suresh
In conclusion, we have developed a solvent-free method
for the facile regeneration of aldehydes from their bisul¢te
addition products in the solid state using montmorillonite
KSF clay under microwave irradiation.
Kumar and J. S. Yadav, Synth. Commun., 1997, 27, 1327;
R. S. Varma, R. Dahiya and S. Kumar, Tetrahedron Lett.,
1
997, 38, 2039; G.-S. Zhang, D-H. Yang, M-F. Chen and
K. Cai, Synth. Commun., 1998, 28, 2221; R. S. Varma, K.
P. Naicker and P. J. Liesen, Tetrahedron Lett., 1998, 39, 3977.
P. Laszlo and A. Mathy, Helv. Chim. Acta, 1987, 70, 577.
A. Cornelis, A. Gerstmans, P. Laszlo, A. Mathy and I. Zieba,
Catal. Lett., 1990, 6, 103.
We thank the CSIR, the UGC, New Delhi and the Uni-
versity of Calcutta for ¢nancial support.
7
8
9
0
H. M. Meshram, Synth. Commun., 1990, 20, 3253.
D. Villemin, B. Labiad and Y. Ouhilal, Chem. Ind., 1989, 607.
Received, 11th January 1999; Accepted, 1st June 1999
Paper E/9/00309F
1
11 R. S. Huber and G. B. Jones, J. Org. Chem., 1992, 57, 5778;
G. B. Jones, R. S. Huber and S. Chau, Tetrahedron, 1993,
4
9, 369.
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2