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Lewis‐Acid‐Mediated Stereospecific Radical Polymerization of Acrylimides Bearing Chiral Oxazolidinones
Author(s) -
Fujita Takehiro,
Yamago Shigeru
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504184
Subject(s) - tacticity , diad , polymerization , lewis acids and bases , selectivity , polymer chemistry , radical polymerization , stereospecificity , chemistry , polymer , catalysis , organic chemistry , copolymer
Lewis acid (MgBr 2 )‐catalyzed radical polymerization of acrylimides bearing chiral oxazolidinones gave highly isotactic polyacrylimides with up to >99 % meso tetrad ( mmm ) selectivity. Polymerization in the absence of Lewis acid gave atactic polymers with 80 % racemo diad ( r ) selectivity; the selectivity was deliberately tuned from 80 % r to >99 % mmm by varying the polymerization conditions. The polyacrylimide was quantitatively converted to corresponding polyacrylates while preserving the stereoregularity, thus providing a general method for the synthesis of atactic to isotactic polyacrylates.