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Highly diastereoselective synthesis of novel polymers via tandem Diels–Alder–ene reactions
Author(s) -
Mallakpour Shadpour E,
Hajipour AbdolReza,
Mahdavian AliReza,
Rafiemanzelat Fatemeh
Publication year - 1999
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/(sici)1097-0126(199902)48:2<109::aid-pi103>3.0.co;2-n
Subject(s) - thionyl chloride , chemistry , acryloyl chloride , polymerization , ene reaction , isoeugenol , chloride , derivative (finance) , dicarboxylic acid , specific rotation , polymer chemistry , succinic anhydride , triethylamine , organic chemistry , yield (engineering) , monomer , polymer , materials science , eugenol , acrylate , financial economics , economics , metallurgy
Cis ‐9,10‐dihydro‐9,10‐ethanoanthracene‐11‐12‐dicarboxylic acid anhydride (1) was converted into its amic acid derivative by reaction with L ‐leucine. The cyclization reaction was carried out in situ using triethylamine to give the succinic imide‐acid derivative (2). Compound (2) was converted to the acid chloride (3) by reaction with thionyl chloride. The reaction of acid chloride (3) with isoeugenol (4) was carried out in chloroform and a novel optically active isoeugenol ester derivative (5) was obtained in high yield. 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione (PhTD) (6) was allowed to react with compound (5). The reaction is very fast and gives only one diastereoisomer of (7) via Diels–Alder and ene pathways in quantitative yield. Compound (7) was characterized by 1 H NMR, IR, specific rotation and elemental analysis, and was used as a model for the polymerization reactions. The polymerization reactions of compound (5) with bis‐triazolinediones (8), (9) were performed in N , N ‐dimethylacetamide (DMAc) at room temperature. The reactions are exothermic and fast, and give novel optically active polymers. Some physical properties and structural characterizations of these new polymers have been studied, and are reported. © 1999 Society of Chemical Industry