101089-45-6Relevant articles and documents
Advanced Polymers from Simple Benzoxazines and Phenols by Ring-Opening Addition Reactions
Deliballi, Zeynep,Kiskan, Baris,Yagci, Yusuf
, p. 2354 - 2361 (2020)
Simple benzoxazines were mixed and reacted with various phenolics such as phenol, p-nitrophenol, p-cresol, 1,3-dihyroxybenzene (resorcinol), 1,3,5-trihydroxybenzene (phloroglucinol), and N-(2-hydroxyphenyl)benzamide. The influence of these phenolic compou
Cationic polybenzoxazines. a novel polyelectrolyte class with adjustable solubility and unique hydrogen-bonding capabilities
Sawaryn, Christian,Landfester, Katharina,Taden, Andreas
, p. 7668 - 7674 (2011)
This article fuses the world of benzoxazine chemistry with the field of polyelectrolyte chemistry and introduces a new approach toward water-soluble polybenzoxazines. The synthesis of a novel class of polybenzoxazine-based polyelectrolytes carrying cation
Insight into the Mechanism of Reversible Ring-Opening of 1,3-Benzoxazine with Thiols
Urbaniak, Tobias,Soto, Marc,Liebeke, Manuel,Koschek, Katharina
, p. 4050 - 4055 (2017/04/27)
The reversible ring-opening addition and fragmentation reaction of p-cresol-based N-phenylbenzoxazine with aliphatic and aromatic thiols was investigated in solvent-mediated and solvent-free reactions. Independently of the used thiol, N-phenylbenzoxazine and the thiols reacted to equilibrium with comparable amounts of reactants and products in aprotic solvent, whereas in protic solvent almost full conversions were reached. In contrast, thiol reactivity was a crucial factor in solvent-free reactions yielding fast and complete conversions for a more acidic thiol and balanced equilibrium concentrations in case of thiols with high pKa values. The strong influence of thiols with low pKa values emphasizes the relevance of the protonation step in the ring-opening reactions of 1,3-benzoxazines with thiols in absence of solvents where acidity predominates nucleophilicity. The reverse reactions, namely adduct dissociation and benzoxazine recovery, were successfully conducted at elevated temperatures and reduced pressure facilitated by the removal of the formed thiols yielding up to 95% recovered 1,3-benzoxazine. These results provide deeper understanding of the reversible ring-opening reaction mechanism of 1,3-benzoxazine with thiols.