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High yield synthesis of fluorinated benzoxazine monomers and their molecular characterization

机译：氟化苯并恶嗪单体的高产率合成及其分子表征

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摘要

A method for the synthesis of 3,4-dihydro-3-pentafluorophenyl-2H-1,3-benzoxazine in a high yield derived from pentafluoroaniline is described. This fluorinated benzoxazine monomer has been developed as a potential precursor for a polybenzoxazine in electronic applications as well as others taking advantage of the low dielectric constant, low flammability, low refractive index, low coefficient of friction, and high glass transition temperature of fluorinated compounds. The traditional benzoxazine synthesis conditions are inappropriate for the synthesis of fluorinated benzoxazines when the fluorination is on the primary amine component. It is found that the pH value of the reaction medium is the controlling factor in the yield of the compound from weak amines. A strongly acidic condition is necessary for the synthesis of similar compounds from other overy weak amines having a pK_a lower than 3. A dramatic increase in the yield of benzoxazinr ring has been observed when benzoxazines with very weak amines are amines are synthesized ina n acidic medium. The effects of solvent and pK_a of phenol are also discussed. The synthesized compounds have been characterized by ~1H NMR, FTIR, GPC and HPLC.
机译：描述了一种高产率地衍生自五氟苯胺的3,4-二氢-3-五氟苯基-2H-1,3-苯并恶嗪的合成方法。这种氟化苯并恶嗪单体已被开发为电子应用中聚苯并恶嗪的潜在前体，并利用了氟化物的低介电常数，低易燃性，低折射率，低摩擦系数和高玻璃化转变温度等优点。当氟化在伯胺组分上时，传统的苯并恶嗪合成条件不适用于氟化苯并恶嗪的合成。发现反应介质的pH值是弱胺化合物的产率的控制因素。从其他过弱的pK_a小于3的过弱胺合成相似的化合物必须具有强酸性条件。当在弱酸性介质中合成具有非常弱胺的苯并恶嗪时，已观察到苯并嗪环的收率急剧增加。 。还讨论了溶剂和苯酚的pK_a的影响。合成的化合物已通过1H NMR，FTIR，GPC和HPLC进行了表征。

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