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Study on 1‐4 cycloaddition reaction. I. Synthesis and optimization of new adduct using Diels–Alder reaction
Author(s) -
Mazroua Azza M.,
Youssif M. A.
Publication year - 2003
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.12064
Subject(s) - cycloaddition , diels–alder reaction , adduct , diene , yield (engineering) , chemistry , molar ratio , bicyclic molecule , polymer chemistry , organic chemistry , materials science , catalysis , composite material , natural rubber
The present investigation has been achieved in accordance with the Diels–Alder reaction (1,4 cycloaddition) to produce a new halogenated bicyclic adduct. ortho ‐Bromoallylbenzoate is a new dienophile that was prepared in a pure form, and its structure was confirmed. The Diels–Alder syntheses of hexachlorocyclopentadiene and the new dienophile were studied to determine the optimum condensation reaction conditions under a temperature range of 90–160°C, reaction times of 1–8 h, and molar diene/dienophile ratios from 1:1 to 5:1 as a consequence. The optimum conditions reached were a temperature of 140°C, an initial diene/dienophile molar ratio of 3:1, and a duration time of 6 h. The maximum stoichometric yield under these optimum conditions (82.5%) was obtained. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 89: 2331–2338, 2003