A polar ester-functionalized aliphatic polysulfone with an odd-number
of linking carbon atoms possessing remarkable thermal stability, degra
ding at 100 degrees C above previously prepared polysulfones, was prep
ared in conjunction with the proposal of a novel concept for polar org
anic polymers. The synthesis involved polyaddition of vinyl sulfone an
d tert-butyl ethyl malonate in the presence of an amidine base and cat
alytic amount of water, followed by decarbo-tert-butoxylation. The pol
ymers were characterized by infrared and nuclear magnetic resonance sp
ectroscopies, elemental analysis, gel permeation chromatography, diffe
rential scanning calorimetry, and thermogravimetric analysis. Characte
rization results compared well with model compounds. Poly-decarbo-tert
-butoxylation was achieved by exposure to trifluoroacetic acid, follow
ed by treatment with copper(I) oxide, affording a soluble polar polysu
lfone, which could be cast into homogeneous films.