ISSN:
0887-624X
Keywords:
ozonolysis
;
polystyrene
;
poly(styrene-co-butadiene)
;
telechelic oligomer
;
supported reagent
;
degradation
;
amide
;
sacrificial
;
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Polystyrene and a poly(styrene-stat-butadiene) have been reacted with ozone in various solvents to establish the conditions necessary for the production, from the latter, of telechelic oligostyrenes having high and controllable end group functionalities. Polymeric ozonides produced by ozonolysis of poly(styrene-stat-butadiene)s, on workup with sodium borohydride or zinc/acetic acid, give dihydroxy- or dialdehyde-ended oligostyrenes, respectively. Workup with borane gives oligomers with a mixture of hydroxy and aldehyde end groups. Oxidative workup with selenium dioxide/hydrogen peroxide yields carboxylic acid-ended oligostyrenes. Workup with polymer-supported reducing or oxidizing agents was less successful. It is shown that side reactions associated with the synthesis of telechelic oligostyrenes by the ozonolysis route, i.e., attack at the α position and possibly also on the phenyl rings of the styrene units, can be minimized by the use of N-dialkyl amides, particularly dimethylacetamide, as sacrificial ozone scavengers. © 1996 John Wiley & Sons, Inc.
Additional Material:
10 Ill.
Type of Medium:
Electronic Resource
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