ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of 2-Alkoxy Substituted Oligo- and Poly(1,4-phenyleneethylene)s and 2-Arylbenzo[b]furanes by Applying the Siegrist ReactionAlkylation of 2-hydroxy-4-methylbenzaldehyde (1) yields the 2-alkoxy-4-methylbenzaldehydes (2a-l) which can be easily transformed to the Schiff bases 3a-l. The intermolecular self-condensation in a strongly alkaline medium leads to the oligo- and poly(1,4-phenyleneethenylene)s (4a-i) with an outstanding regular constitution and overall (E)-configuration. The terminal N-arylamino group can be cleaved by hydrolysis generating the compounds 5a-i. An intramolecular condensation forming the benzo[b]furanes 6j,k is observed for 3j,k - due to the activated OCH2 group in 2-position. Finally, both the 4-CH3 as well as the 2-OCH2 group take part in the reaction of 3l. The twofold Schiff base 3m, obtained from 1 via 2m, yields the ladder polymer 7m.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19943360205
