ISSN:
0360-6376
Keywords:
Physics
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction course of 1-(N-phenyl-carbamyl)aziridine with NaI was found to be highly sensitive to the nature of solvent used; e.g., acetone preferentially gives 1-phenyl-2-imidazolidinone, whereas dimethylformamide (DMF) gives 2-anilino-2-oxazoline. Nuclear magnetic resonance (NMR) study of the solvent effect revealed the relation between the site in the aziridine compound, with which the solvents interact, and the reaction products. From the results obtained by these ring-transformation studies, the use of diethyl sulfate, which is expected to solvate simultaneously at the carbonyl oxygen and the carbamyl-nitrogen atoms, resulted in polymerization of the monomer selectively to the oligomer of type - [CH2CH2N(CONHPh)]n - . The diethyl sulfate was shown to play dual roles as a solvating reagent and an initiator. The oligomer obtained includes relatively definite amount (one molecule per ca. four monomer units) of diethyl sulfate in the “washed” state. The absorbed diethyl sulfate can be removed by treating with aqueous NaOH solution or Amberlite-400 column elution without altering the chemical constitution of the backbone in the polymer. Application of the polymerization procedure to several N-alkyl substituted monomers resulted in oligomers of a similar type. The difference in the monomer reactivity depending on the nature of the substituent groups can be due mainly to steric factors.
Additional Material:
10 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/pol.1978.170160515
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