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Synfacts 2025; 21(07): 685
DOI: 10.1055/a-2601-5152
DOI: 10.1055/a-2601-5152
Synthesis of Materials and Unnatural Products
Stereocontrolled Poly(vinyl alcohol) from Tailored Vinylboron
Suzuki H,
Nishikawa T *,
Ouchi M *.
Kyoto University, Japan
Design of Vinylboron Monomers for the Comprehensive Structural Control of Poly(vinyl alcohol)s via Stereospecific Controlled Radical Polymerization and Subsequent Side-Chain Replacement.
J. Am. Chem. Soc. 2025;
147: 12672-12685
DOI: 10.1021/jacs.5c00336
Design of Vinylboron Monomers for the Comprehensive Structural Control of Poly(vinyl alcohol)s via Stereospecific Controlled Radical Polymerization and Subsequent Side-Chain Replacement.
J. Am. Chem. Soc. 2025;
147: 12672-12685
DOI: 10.1021/jacs.5c00336
Keywords
poly(vinyl alcohol) - vinylboron - stereospecific radical polymerization - post-polymerization oxidation
Significance
Linear poly(vinyl alcohol)s with controlled tacticity are achieved via radical-polymerization of vinylborons, followed by oxidation. The specially designed substituents on boron effectively suppress the backbiting and realize the stereoselectivity through steric effects.
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Comment
The polymerizations proceed via a free-radical mechanism, and the steric features of the N-alkyl substituents on the anthranilamide, a protective group for the boron, are responsible for controlling the tacticity, presumably by inducing a helical conformation.
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Publication History
Article published online:
23 June 2025
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