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首页> 外文期刊>The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory >Thermally Induced Sigmatropic Isomerization of Pseudosaccharyl Allylic Ether
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Thermally Induced Sigmatropic Isomerization of Pseudosaccharyl Allylic Ether

机译：伪糖基烯丙基醚的热诱导正向异构化

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摘要

The thermally induced sigmatropic isomerization of the pseudosaccharyl allylic ether [3-(allyloxy)-1,2- benzisothiazole 1,1-dioxide; ABID] has been investigated by a multidisciplinary approach using temperature dependent infrared spectroscopy, differential scanning calorimetry, and polarized light thermomicroscopy, complemented by theoretical methods. Migration of the allylic system from O to N occurs in the melted ABID, and the thermally obtained 2-allyl-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (ABIOD) starts to be produced at ca. 150 °C, in a process with an activation energy of ～92 kJ mol-1. From kinetic data, a concerted [3,3′] sigmatropic mechanism is proposed. In the temperature range investigated, ABIOD was found to exhibit polymorphism. Cooling of the molten compound leads to the production of a metastable crystalline form, which upon annealing at room temperature might be transformed to the stable crystalline phase. ABID shows a single crystalline variety. Assignments were proposed for the infrared spectra of the observed neat condensed phases of the two compounds.
机译：假糖基烯丙基醚[3-（烯丙氧基）-1，2-苯并异噻唑1，1-二氧化物的热诱导σ异构化; [ABID]已通过多学科方法进行了研究，使用了依赖温度的红外光谱，差示扫描量热法和偏振光热显微镜，并辅以理论方法。烯丙基体系从O迁移到N的过程是在熔融的ABID中发生的，大约在30℃开始生产热获得的2-烯丙基-1，2-苯并噻唑-3（2H）-1，1-二氧化物（ABIOD）。 150°C，活化能〜92 kJ mol-1。根据动力学数据，提出了一种协调的[3,3']σ机制。在研究的温度范围内，发现ABIOD具有多态性。熔融化合物的冷却导致产生亚稳态的结晶形式，该结晶形式在室温下退火后可能转变为稳定的结晶相。 ABID显示单一晶体品种。提出了分配给观察到的两种化合物的纯净冷凝相的红外光谱。

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