Silica–PSCl3
4109
ACKNOWLEDGMENT
The authors thank S. K. Sekhar, director, Defense Research and Development
Establishment (DRDE), for his keen interest and encouragement.
REFERENCES
1. (a) Bernardi, F.; Csizmadia, I. G.; Mangini, A., Eds.; Organic Sulfur Chemistry;
Elsevier: Amsterdam, 1985; (b) Damani, L. A. ed. Sulfur-containing drugs
and
related
organic
compounds:
Chemistry,
Biochemistry
and
Toxicology; Harwood, E. Ed.; Chichester, England, 1989; (c) Pathak, U.;
Raza, S.; Kulkarni, A. S.; Vijayaraghavan, R.; Kumar, P.; Jaiswal, D. K. Novel
S-substituted aminoalkylamino ethanethiols as potential antidotes against sulfur
mustard toxicity. J. Med. Chem. 2004, 47, 3817.
2
3
. Solladie, G. Synthesis of sulfides, sulphoxide, and sulfones. In Comprehensive
Organic Synthesis; Trost, B. M. and Fleming, I. Eds.; Pergamon Press: Oxford,
U. K., 1991, Vol. 6, pp. 130–170.
. (a) Page, B. P. C.; Wilkes, R. D.; Reynolds, D. In Comprehensive Organic Func-
tional Group Transformations, 1st Edn.; Katritzky, A. R., Cohn, O. M. and
Rees, C. W. Eds.; Elsevier: Oxford, 1995, Vol. 2 Section 2.03; (b) Procter, D. J.
The synthesis of thiols, selenols, sulfoxides, selenides, sulfoxides, selenoxides,
sulfones and selenones. J. Chem. Soc. Perkin Trans. 1 1999, 641–667;
(c) Procter, D. J. The synthesis of thiols, selenols, sulfoxides, selenides, sulfoxides,
selenoxides, sulfones and selenones. J. Chem. Soc. Perkin Trans. 1 2001, 335–354.
. Miller, S. J.; Collier, T. R.; Weiming, W. Efficient reduction of sulfoxides with 2,
4
5
6-dihydroxypyridine. Tetrahedron Lett. 2000, 41, 3781–3783.
. Nakayama, J.; Tai, A.; Iwasa, S.; Furuya, T.; Sugihara, Y. Tetracyanoethylene
oxide not only oxidizes sulfides to sulfoxides but also reduces sulfoxides to
sulfide. Tetrahedron Lett. 2005, 461, 1395–1397.
6
7
8
. Iranpoor, N.; Firouzabadi, H.; Jamalian, A. Deoxygenation of sulfoxides and
reductive coupling of sulfonyl chlorides, sulfinates and thiosulfonates using
[
PCl3-n(SiO
. Fernandes, A. C.; Romao, C. C. A novel method for the reduction of sulfoxides and
pyridine N-oxides with the system silane/MoO Cl . Tetrahedron 2006, 62,
650–9654.
. (a) Olah, G. C.; Gupta, B. G. B.; Narang, S. C. Synthetic methods and reactions;
2 n
) ] as a heterogeneous phosphine reagent. Synlett 2005, 9, 1447–1449.
2
2
9
1
5
4: Deoxygenation of sulfoxides and azoxides with tris(dimethylamino)pho-
sphine/Iodine/sodium iodide reagent. J. Org. Chem. 1978, 43, 4503–4505;
b) Denis, J. N.; Krief, A. Phosphorus tri-iodide (PI ), a powerful deoxygenating
(
3
agent. J. Chem. Soc. Chem. Com. 1980, 544–545; (c) Vozza, J. F. Deoxygenation
and chlorination of azoxybenzene by acidic halides. J. Org. Chem. 1969, 34,
3219–3220; (d) Castrillon, J. P. A.; Szmani, H. H. J. Reduction of sulfoxides by
triphenylphosphine and carbon tetrachloride. J. Org. Chem. 1965, 30, 1338.
. Sanz, R.; Escribano, J.; Aguado, R.; Pedrosa, M. R.; Arnaiz, F. J. Selective de-
oxygenation of sulfoxides to sulfides with phosphate catalysed by dichlorooxo-
molbdenum (VI). Synthesis 2004, 1629.
9
10. Smith, K., ed. Solid Supports and Catalysts in Organic Synthesis; Harwood, E. and
PTR Prentice Hall: New York and London, 1992.
11. Clark, J. H.; Kybett, A. P.; Macquarrie, D. J. Suported Reagents: Preparation,
Analysis and Applications; VCH: New York, 1992.