Polystyrene-supported (4-phenylseleno)morpholine was synthesised and could be used as an efficient α-selenenylating agent for saturated aldehydes; subsequent oxidation of polystyrene-supported α-selenoaldehydes and the products from the Wittig reaction of them with chloromethylidenetriphenylphosphorane with an excess of 30% hydrogen peroxide at room temperature afforded α,β-unsaturated aldehydes in good yields and purities.
For recent reviews on SPOS, see: (a) FruchtelJ.S., and JungG., Angew. Chem. Int. Ed., 1996, 35, 17; (b) P. H. H. Hermkens, H. C. J. Ottenhijm and D. C. Rees, Tetrahedron, 1997, 53, 5643; (c) R. C. D. Brown, J. Chem. Soc., Perkin Trans. 1, 1998, 3293; (d) B. A. Lorsbach and M. J. Kurth, Chem. Rev., 1999, 99, 1549; (e) F. Guillier, D. Orain and M. Bradley, Chem. Rev., 2000, 100, 2091; (f) R. E. Sammelson and M. J. Kurth, Chem. Rev., 2001, 101, 137.
2.
(a) LerougeP., and PaulmierC., Bull. Soc. Chim. Fr., 1985, 1219. Related α-selenenylating agent for aldehydes, see: (b) H. J. Reich and J. M. Renga, J. Org. Chem., 1975, 40, 3313; (c) M. Jefson and J. Meinwald, Tetrahedron Lett., 1981, 22, 3561.
3.
PaulmierC., Ed., Selenium reagents and intermediates in organic synthesis, Pergamon Press, Oxford, 1986.
4.
SharplessK.B., LauerR. F., and TeranishiA. Y., J. Am. Chem. Soc., 1973, 95, 6137.
5.
HuangX., and ShengS.-R., Tetrahedron Lett., 2001, 42, 9035.
6.
ShengS.-R., and HuangX., J. Chem. Res.(S), 2002, 184.
7.
NicolaouK.C., PastorJ., BarluengaS., and WinssingerN., Chem. Commun., 1998, 1947.
8.
FarrallM.J., and FrechetJ. M. J., J. Org. Chem., 1976, 41, 3877.