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Chirality induction in cyclocopolymerization of bis( p ‐vinylbenzoate)s of carbohydrates with styrene: Chiroptical study of resulting polymer by exciton chirality method
Author(s) -
Haba Osamu,
Yokota Kazuaki,
Kakuchi Toyoji
Publication year - 1995
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530070403
Subject(s) - chemistry , chirality (physics) , styrene , cotton effect , optical rotation , absolute configuration , specific rotation , copolymer , circular dichroism , monomer , axial chirality , stereochemistry , polymer , polymer chemistry , crystallography , organic chemistry , catalysis , enantioselective synthesis , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Abstract Three bis( p ‐vinylbenzoate) monomers, 2,3‐ O ‐isopropylidene‐1,4‐bis‐ O ‐( p ‐vinylbenzoyl)‐L‐threitol (BIT), methyl 4,6‐ O ‐isopropylidene‐2,3‐bis‐ O ‐( p ‐vinylbenzoyl)‐α, D ‐glucopyranoside (BIG), and 1,2:5,6‐di‐ O ‐isopropylidene‐3,4‐bis‐ O ( p ‐vinylbenzoyl)‐D‐mannitol (BIM), were prepared and cyclocopolymerized with styrene. The resulting copolymers were hydrolyzed with KOH to remove the chiral template, and treated with diazomethane to give poly[(methyl p ‐vinylbenzoate)‐ co ‐styrene] [poly(MVB‐ co ‐St)]. All the poly(MVB‐ co ‐St) had a specific rotation and their CD spectra exhibit a split Cotton effect. Poly(MVB‐ co ‐St) derived from poly(BIT‐ co ‐St) showed a positive Cotton effect at 255 nm and a negative one at 235 nm. According to the exciton chirality method, poly(MVB‐ co ‐St) possessed negative chirality, and the stereochemistry of the carbon atom attached to the 4‐benzoyl group had the S configuration. The absolute configuration of poly(MVB‐ co ‐St) was determined as R for the BIG/St system and S for the BIM/St system. © 1995 Wiley‐Liss, Inc.