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Deuterium labelling of poly((dimethyliminio)alkylenes)
Author(s) -
Westermark B.
Publication year - 1988
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580251212
Subject(s) - chemistry , halogenation , reductive amination , acetic acid , adipic acid , medicinal chemistry , carboxylic acid , hexamethylenediamine , succinic acid , polymer chemistry , nuclear chemistry , organic chemistry , catalysis , polyamide
Abstract Selectively deuterated monomers for preparation of deuterated poly((dimethyliminio)propylene), poly((dimethyliminio)hexylene), and poly((dimethyliminio)decylene) have been synthesized:(2‐ 2 H 2 )‐1,3‐dibromopropane, (2,5‐ 2 H 2 )‐1,6‐dibromohexane, (1,10‐ 2 H 2 )‐, (2,9‐ 2 H 2 )‐, and (4,7‐ 2 H 2 )‐1,10‐dibromodecane and N,N,N′,N′‐tetra‐( 2 H 2 )‐methyldecamethylenediamine. The syntheses of all dibromoalkanes involved a carboxylic acid or a carboxylic acid derivative either as starting compound or as an intermediate. (2‐ 2 H 2 )‐1,3‐Dibromopropane was synthesized from catalytically exchanged (NaO 2 H/ 2 H 2 O) diethylmalonate by reduction with lithium aluminium hydride and bromination with HBr. (2,5‐ 2 H 2 )‐1,6‐Dibromohexane and (2,9‐ 2 H 2 )‐1, 10‐dibromodecane were prepared from base‐catalytically (NaO 2 H/ 2 H 2 O, 160°C) exchanged sodium salts of adipic and succinic acids, respectively, followed by reduction (LiA1H 4 ) and bromination (HBr). (1,10‐ 2 H 2 )‐1,10‐Dibromodecane was prepared from succinic acid by reduction with LiA1 2 H 4 and subsequent bromination. (4, 7‐ 2 H 2 )‐1,10‐Dibromodecane was synthesized by coupling the lithiooxazoline salt of acetic acid with (2,5‐ 2 H 2 )‐1,6‐dibromohexane followed by synthetic steps analogous to those above. The synthesis of N,N,N′,N′‐tetra‐( 2 H 2 )‐ methyldecamethylenediamine was achieved by reductive amination between hexamethylenediamine and perdeuteroformaldehyde.