The first part of this thesis describes a novel liquid phase synthesis method for this class of oligomeric compounds by the so-called hydrophobic anchoring group- or hydrophobic tag method. The hydrophobic anchoring groups used for this purpose here are aromatic molecules on the basis of benzyl alcohol or benzhydrylamine, which are attached to long alkyl chains that determine the solubility behavior of the group itself as well as that of the oligomeric compounds attached to it. As a consequence, the reaction steps necessary for the oligomerization can be performed as liquid phase reactions in non-polar solvents, while the intermediate products precipitate from polar solvents, and thus, the work-up is greatly simplified. Furthermore, we also synthesized novel monomers with the alternative 2-(4-nitrophenyl)sulfonylethoxycarbonyl (Nsc) protecting group for the application in the established solid phase synthesis protocols. Due to the unique properties of this protection group used in these monomers, very mild conditions can be employed for its deprotection. These mild conditions can potentially help to reduce the extent of base-induced side-reactions and improve the overall synthesis quality of such solid phase protocols. This in turn would reduce the time and effort needed for the purification and also substantially reduce the overall cost of the synthesis.
The second part of this work deals with a polymeric phosphine reagent based on a polyphosphazene backbone. In conjunction with hexachloroethane, this reagent was efficiently applied in the chlorination of alcohols under Appel-conditions. In contrast to non-polymeric reagents, the side-product stemming from the described polymeric reagent is efficiently removed by easy work up-steps such as precipitation and filtration, thus, avoiding tedious chromatographic separations which are usually necessary with non-polymeric reagents. In comparison to other polymeric reagents, the reagent proved to be highly reactive and to be capable of converting a wide variety of alcohols to their corresponding chlorides in high yields and low reaction times. Moreover, it could also be shown that this polymeric reagent could be recovered almost quantitatively and could be efficiently re-used by re-chlorination with oxalyl chloride.