96326-39-5Relevant articles and documents
Regioselective ring-emitting esterification on azacyclohexane quaternary salts: A DFT and synthetic study for covalent fixation of electrostatic polymer self-assemblies
Kimura, Akihiro,Takahashi, Shinnosuke,Kawauchi, Susumu,Yamamoto, Takuya,Tezuka, Yasuyuki
, p. 3086 - 3094 (2013/06/05)
A regioselective nucleophilic esterification upon six-membered, thus considered unstrained, azacyclohexane quaternary salts has been disclosed by DFT calculations using a model compound and subsequent experimental studies of nucleophilic substitution on N-phenyl-3,3-dimethylpiperidinium salt groups at the polymer chain ends by carboxylate anions. An exclusive ring-emitting esterification was proposed theoretically and confirmed experimentally to produce a simple ester group, in contrast to less robust amino-ester linkages through an alternative ring-opening process with strained five-membered ammonium salts. This reaction was subsequently applied to a prototypical process of an electrostatic self-assembly and covalent fixation (ESA-CF) technique to produce a ring polymer having simple ester linking units.