The polymerization of 4-hydroxy-N-propargylpiperidine, having 4-hydroxypipe
ridine moiety, was carried out with various transition metal catalysts. The
polymerizations proceeded well to give a relatively high yield of polymer
(maximum polymer yield: 93%). Palladium, platinum, and ruthenum chlorides w
ere found to be generally effective for this polymerization. On the other h
and, the group 5 and 6 transition metal catalysts such as WCl6, MoCl5, WCl6
-organoaluminum compounds etc. fail to polymerize this monomer. The molecul
ar structure of the resulting poly(4-hydroxy-N-propargylpiperidine) was cha
racterized by the various instrumental analysis methods such as NMR (H-1- a
nd C-13-), IR, and UV-visible spectroscopies. The IR spectrum of polymer sh
ows neither the acetylenic hydrogen stretching (3197 cm(-1)) nor the carbon
-carbon triple bond stretching (2113 cm(-1)) frequencies presented in the I
R spectrum of monomer. Instead, the carbon-carbon double bond stretching fr
equency at 1611 cm(-1) was newly observed. These polymers were mostly brown
and black powders and were completely soluble in such polar solvents as fo
rmic acid, DMF, DMSO, and tetrahydrofuran. X-ray diffraction analysis of th
e resulting poly(4-hydroxy-N-propargylpiperidine) revealed that this polyme
r is mostly amorphous.