Abstract
Five new (Z)-2-alkoxyvinyl acetates (isopropyl, butyl, hexyl, decyl, and 10-undecenyl derivatives) have been prepared by a retro-Diels-Alder technique. The synthesis of typical detergent derivatives with long alkyl residues is markedly improved by using cyclopentadiene instead of anthracene for the Diels-Alder reaction. Amphiphilic polymers were obtained by cationic homopolymerization of the long-chain derivatives. As a result of their molecular arrangement, these polymers show a decidedly hydrophobic character. However, a highly water-soluble polymer with detergent properties resulted if the amphiphilic geometry of the homopolymer of the 10-undecenyl derivative was changed by oxidative cleavage of the terminal side-chain double bond.
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