ON THE CHIRALITY OF POLYVINYL COMPOUNDS .16. OPTICAL-ACTIVITY OF COPOLYMERS CONSISTING OF DISTYRYL DIADS ALTERNATING WITH SUBSTITUTED MALEIMIDE OF MALEIC-ANHYDRIDE UNITS
G. Wulff et S. Krieger, ON THE CHIRALITY OF POLYVINYL COMPOUNDS .16. OPTICAL-ACTIVITY OF COPOLYMERS CONSISTING OF DISTYRYL DIADS ALTERNATING WITH SUBSTITUTED MALEIMIDE OF MALEIC-ANHYDRIDE UNITS, Macromolecular chemistry and physics, 195(11), 1994, pp. 3665-3677
The copolymerization of 3,4-O-cyclohexylidene-D-mannitol 1,2:5,6-bis-O
-[(4-vinylphenyl)-boronate] (M1) with different N-substituted maleimid
es and with maleic anhydride has been studied. These monomers copolyme
rize in 1:1 proportion, yielding after removal of the temple (3,4-O-cy
clohexylidene-D-mannitol) copolymers with bis(4-vinylphenylboronic aci
d) diads alternating with the other comonomeric unit. By deboronation
these diads can be transformed to distryl diads. These diads possess p
redominantly (S,S)-configuration; thus optically active copolymers wit
h main-chain chirality were produced. The chiroptical properties (opti
cal rotation and circular dichroism) of the copolymers were studied. C
orresponding copolymers with maleic anhydride units can easily be tran
sformed by polymer analogous reaction with nucleophiles, as was exempl
ified by alcoholysis with fatty alcohols.