Reduction of the 2‐azetidinone moiety in the polymer main chain: A novel synthetic route to polyamine with hydroxymethyl pendant

A polymer with a 2‐azetidinone moiety in its main chain was efficiently synthesized by [2 + 2] cycloaddition of bisimine with bisketene. The bisketene was easily prepared by dehydrochlorination of the corresponding dicarboxylic acid chloride and was used without purification. The treatment of the obtained polymer with lithium aluminum hydride resulted in a reductive ring‐opening reaction of the 2‐azetidinone moiety in the main chain that gave the corresponding linear polyamine with hydroxymethyl side chains. © 2001 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 39: 3789–3796, 2001     

Synthesis of aromatic polyesters and polyamides by alternating copolymerizations of 1,4-dicarbonyl-1,4-dihydronaphthalene with bezoquinones and benzoquinone diimines

1,4-Dicarbonyl-1,4-dihydronaphthalene ( 1 ) was synthesized by the dehydrochlorination reaction of 1,4-dihydronaphthalene-1,4-dicarbonyl chloride with triethylamine and obtained as its very dilute solution, but it easily polymerized in the concentration as high as 0.1 mol/L to give its polymer. 1 generated in situ by the dehydrochlorination reaction of 1,4-dihydronaphthalene-1,4-dicarbonyl chloride in a deoxygenated toluene polymerized alternatingly with benzoquinones such as 2-dodecylthio-p-benzoquinone, 2,5-di(tert-butyl)-p-benzoquinone, p-benzoquinone, and 2,3-dichloro-5,6-dicyano-p-benzoquinone, and with benzoquinone diimines such as N,N′-diethoxycarbonyl-p-benzoquinone diimine, N,N′-dibenzoyl-p-benzoquinone diimine, and N,N′-diphenyl-p-benzoquinone diimine to give aromatic polyesters and polyamides, respectively. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 1929–1936, 1998