Solid-Phase Organic Synthesis Based On Polystyrene Bound Organoselenium Reagents

In this dissertation, solid-phase organic synthesis reaction based on several polystyrene-bound organoselenium reagents were investigated.Firstly, Treatment of the polystyrene-bound α-phenylseleno ketones and esters prepared from 1% cross-linked polystyrene-supported selenium bromide with ketone and ester enolates with 30% hydrogen peroxide afford α,β-unsaturated ketones and esters in good yields and high purities. Reaction of polystyrene-supported selenium bromide with ethene furnished β-bromoethyl selenide resin, which was treated with substituted phenol, followed by oxidation-elimination with 30% peroxide hydrogen at room temperature to afford aryl vinyl ether compounds in good yield and high purity.Secondly, Treatment of polystyrene-supported α-selenopropionic acid and α-selenobutanoic acid with excess thionyl chloride in DCE gave polystyrene-supported α-selenopropanoyl chloride and polystyrene-supported α-selenobutyryl chloride, respectively. After removing excess thionyl chloride, and without further isolation, they were allowed to react with primary and secondary amines in the presence of anhydrous triethylamine to afford corresponding α-selenopropanamide and α-selenobutanamide resin. Subsequent oxidation-elimination with 30% peroxide hydrogen at room temperature furnished acrylamide and 2-butenamide compounds, respectively. The procedure provided a convenient and wild method with good yield and high purity for the preparation of 2-Alkenamide.Finally, 1% cross-linked polystyrene-supported 4-(phenylseleno) morpholine was reacted with α-formylcycioanones and subsequent oxidative deselenation afforded P-dicarbonyl enones compounds in good yields and high purities.