title: Amino-functionalized (meth)acryl polymers by use of a solvent-polarity sensitive protecting group (Br-t-BOC).
abstract: We describe the synthesis of bromo-tert-butyloxycarbonyl (Br-t-BOC)-amino-protected monomers 2-((1-bromo-2-methylpropan-2-yl)oxycarbonylamino)ethyl (meth)acrylate 3a,b. For this purpose, 2-isocyanatoethyl (meth)acrylate 1a,b was reacted with 1-bromo-2-methylpropan-2-ol (2a). The free radical polymerization of (Br-t-BOC)-aminoethyl (meth)acrylates 3a,b yielded poly((Br-t-BOC)-aminoethyl (meth)acrylate) 6a,b bearing protected amino side groups. The subsequent solvolysis of the Br-t-BOC function led to the new polymers poly(2-aminoethyl (meth)acrylate) 8a,b with protonated free amino groups. The monomers and the resulting polymers were thoroughly characterized by (1)H NMR, IR, GPC and DSC methods. The kinetics of the deprotection step was followed by (1)H NMR spectroscopy. The solvent polarity and neighboring group effects on the kinetics of deprotection are discussed.
authors.affiliation: Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Duesseldorf, Universitaetsstraße 1, D-40225 Duesseldorf, Germany.
authors.forename: Helmut
authors.initials: H
authors.lastname: Ritter
authors.affiliation: Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Duesseldorf, Universitaetsstraße 1, D-40225 Duesseldorf, Germany.
authors.forename: Monir
authors.initials: M
authors.lastname: Tabatabai
authors.affiliation: Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Duesseldorf, Universitaetsstraße 1, D-40225 Duesseldorf, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Herrmann
keywords: (meth)acryl polymers; amino group protection; bromo-tert-butyloxycarbonyl; deprotection; free radical polymerization; neighboring group effects; solvent polarity