The 4-methacrylamido-2-methyl-2-butoxy-carbonyl-function as polymerizable amino-protecting group

The synthesis of an highly acidic sensitive polymerizable amino-protecting group is described in the case of the N-protected model compound 4-methacryl-amido-2-methyl-2-butyl-N-p-chlorophenylcarbamate. The new monomer was homopolymerized and copolymerized by radical initiation. Kinetics of acidically induced p-chloroaniline cleavage from the monomer and polymers were followed by NMR spectroscopy. The influence of Calcium-ions and neighbouring group effects are discussed.