Kawaguchi Asei William, Sudo Atsushi, Endo Takeshi
Molecular Engineering Institute, Kinki University, Kayanomori, Iizuka, Fukuoka 820-8555, Japan.
ACS Macro Lett. 2013 Jan 15;2(1):1-4. doi: 10.1021/mz3005296. Epub 2012 Dec 10.
The reversible nature of the addition reaction of 1,3-benzoxazine and thiol at ambient temperature was discovered by investigating the reaction with using -cresol-derived -phenyl benzoxazine and 1-octadecanethiol . The reaction was performed in several deuteriated media involving CDCl and CDCl + CDOD, for monitoring their reaction by H NMR spectrometry. CDCl was a favorable solvent for the efficient progress of the reaction, and its combination with CDOD allowed further acceleration of the reaction. In both cases, the reaction proceeded until conversion of reached a certain ceiling value, to suggest that the reaction was reversible. This reversible nature was concretely confirmed by finding a dissociation reaction of isolated into and in CDCl. Analogously, a bisphenol A-derived bifunctional benzoxazine and 1,6-hexanedithiol underwent the polyaddition in CDCl + CDOD at ambient temperature to afford the corresponding polymer . Successful depolymerization of into small fragments was achieved by dissolving in CDCl.
通过研究对甲酚衍生的对苯基苯并恶嗪与1-十八烷硫醇的反应，发现了1,3-苯并恶嗪与硫醇在室温下加成反应的可逆性质。该反应在几种氘代介质中进行，包括CDCl₃和CDCl₃ + CD₃OD，通过¹H NMR光谱监测它们的反应。CDCl₃是使反应有效进行的有利溶剂，它与CD₃OD的组合可使反应进一步加速。在这两种情况下，反应都进行到转化率达到一定上限值，这表明反应是可逆的。通过在CDCl₃中发现分离出的产物分解为起始原料，具体证实了这种可逆性质。类似地，双酚A衍生的双官能苯并恶嗪与1,6-己二硫醇在室温下于CDCl₃ + CD₃OD中进行聚加成反应，得到相应的聚合物。通过将聚合物溶解在CDCl₃中，成功地将其解聚为小片段。
