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Synthesis of oligomeric chains with 9,10‐dihydroanthracene units by carbanion alkylation
Author(s) -
Bender Dietmar,
Herbst Heinz,
Schade Peter,
Müllen Klaus
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210625
Subject(s) - alkylation , chemistry , deprotonation , electrophile , carbanion , bifunctional , medicinal chemistry , propane , stereoselectivity , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , catalysis , ion
Deprotonation of 9,10‐dihydroanthracene ( 2 ) affords the monoanion 6 which is subjected to alkylation reactions with mono and bifunctional electrophiles. Crucial intermediates in syntheses using 6 are 9‐(3‐bromopropyl)‐9,10‐dihydroanthracene ( 7 ) and 1,3‐bis(9,10‐dihydro‐9‐anthryl)propane ( 9 ) since they provide access to linear oligomers in which 9,10‐dihydroanthracene units are linked by trimethylene groups. The alkylation processes of these species can be extended to the structurally related polymer 4 . The regio‐ and stereoselectivity of the alkylation reactions are investigated by 1 H‐ and 13 C‐NMR spectroscopy.
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