A. Bouzide et al. / Tetrahedron Letters 42 (2001) 8781–8783
8783
by an SN2 displacement of the ditosylate with sodium
azide afforded the corresponding diazide in 85% over-
all yield (Scheme 2).
Coll. Vol. 3, p. 366; (b) Fieser, L. F.; Fieser, M.
Reagents for Organic Synthesis; Wiley: New York, 1967;
Vol. 1, p. 1179; (c) Sandler, S. R.; Karo, W. Organic,
Functional Group Preparations; Academic: New York,
1983; Vol. 1, p. 633.
In conclusion, silver(I) oxide combined with potas-
sium iodide is an efficient reagent system to mediate
sulfonylation of alcohols in high yield under mild
reaction conditions. A key merit of the present
method is its applicability in neutral conditions. Thus,
base- or acid-sensitive substrates are sulfonylated
without detecting any side-products during the course
of the reaction. All compounds were characterized by
NMR, IR and MS and are consistent with the
assigned structures.7
2. Yoshida, Y.; Shimonishi, K.; Sakakura, Y.; Okada, S.;
Aso, N.; Tanabe, Y. Synthesis 1999, 9, 1633.
3. (a) Ouchi, M.; Inoue, Y.; Liu, Y.; Nagamune, S.; Naka-
mura, S. Bull. Chem. Soc. Jpn. 1990, 63, 1260; (b) Fen-
ton, D. E.; Parkin, D. J. Chem. Soc., Perkin Trans. 1
1981, 449; (c) Cornforth, J. W.; Morgan, E. D.; Potts,
K. T.; Rees, R. J. W. Tetrahedron 1973, 29, 1659.
4. (a) Boons, G.-J.; Castle, G. H.; Clase, J. A.; Grice, P.;
Ley, S. V.; Pinel, C. Synlett 1993, 913; (b) Purdie, T.;
Mar-tinelli, M. J.; Nayyar, K. N.; Moher, E. D.; Dhokt,
U. P.; Pawlak, J. M.; Vaidyanathan, R. Org. Lett. 1999,
1, 447.
Acknowledgements
5. (a) Irvine, J. C. J. Chem. Soc. 1903, 83, 1021; (b) Pur-
die, T.; Bridgett, R. C. J. Chem. Soc. 1903, 83, 1037; (c)
Mislow, K. J. Am. Chem. Soc. 1951, 73, 4043.
6. Tanabe, M.; Peters, R. H. Org. Synth. Coll. Vol. VII
1990, 386.
The authors gratefully acknowledge the financial sup-
port of the foundation Armand-Frappier and the
Natural Sciences and Engineering Research Council
(NSERC) of Canada. We would like to thank Dr.
Gervais Berube´ and Ming Chou for comments on the
manuscript.
7. Selected spectral data for the product of entry 13: 1H
NMR (500 MHz, CDCl3): l 1.21 (t, J=7.5 Hz, 3H),
1.51 (d, J=6.0 Hz, 3H), 2.44 (s, 3H), 4.11 (q, J=7.7
Hz, 2H), 4.30 (q, J=6.0 Hz, 1H), 7.34 (d, J=7.5 Hz,
2H), 7.82 (d, 7.5 Hz, 2H); 13C NMR (65 MHz, CDCl3):
l 13.9, 18.4, 21.65, 61.8, 74.1, 128.0, 129.8, 133.4, 145.1,
169.0.
References
1. (a) Wagner, R. B.; Zook, H. D. Synthetic Organic
Chemistry; Horning, E.C., Ed.; Wiley: New York, 1955;