Selectively deuterated monomers for preparation of deuterated po 1 y ( ( dime t h y 1 i m i n i o ) prop y 1 e ne ) , p o 1 y ( ( d i m e t h y 1 i 10 i n i 0 ) hex y 1 c n e ) , and poly((dimethy1iminio)decylene)
have been synthesized:(2-'Y2)-1.3-dibromopropane.
( 1.10-11 2 ) -,
( 2 , 9-2H2 I-, an d (4,7-I1 ) -1 , 1 0-d i b r o m od eca n e and ?4 , N , N' , X Itetra-(2!12)-methyldecamethylenediamine.
T h e s y n t h e s e s o f a l l dibromoalkanes involved a carboxylic acid or a carboxylic acid derivative either as starting compound or as an intermediate.
(2-2H2)-1,3-Dibromopropane w a s synthesized from catalytically exchanged ( Na02H/2i120) diethyl malonate by reduction with 1 it hium aluminium hydride and bromination with HBr. (2,5-2!42)-1,6-Dibromohexane and (2,9-2H2)-1,10-dibromodecane were prepared from base-catalytically (Na02H/21i20, 16OoC) exchanged sodium salts of adipic and succinic acids, respectively, followed by reduction (LiAlH4) and bromination (BBr). (1,10-211~)-1,10-Dibromodecane was prepared f r o m s u c c i n i c a c i d by r e d u c t i o n w i t h L i A 1 2 Y b a n d subsequent w a s synthesized by coupling the lithiooxazoline salt of acetic acid with (2,5-2112)-1,6-dibromohexane followed by synthetic steps analosous to those above. The synthesis of ~,N.S',C'-tetra-(2112)nethyldecamethylenediamine w a s achieved by reductive amination he t ween hexa met h y 1 en e d i a m i ne an (I per de ti t e r o f or m A 1 d e h y d e. (2, 5-2 H2)-l, 6-d i b r o m o hexane , br o m i na t i on. (4,7 -11 2) -1,lO-D i br o m od e c a n e Key words: poly((dimethyliminio)alkylenes), (2-2112)-1,3-dibro710propane, ( 2 , 5 -2 : 1 2 ) -1 , 6 -d i b r o n o h e x a n e , (l,10-2~~2)-l,10-di bromodecane, (it 7 -' I., -) -1, lo-:' i r o * * odeca ne , ?4 , N , ! 4 I, !it-t e t r a -( !! )-m e t h y 1 d e c a m e t 11 y 1 e n e tl i n .? i II c'
( 2 . 9 -2!!2)-1.1O-cl i b r o-nod e c n ne , 0362-4803/88/121381-11SOS.M 0 1988 by Joha Wiley & Soas, Ltd.