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Photochemistry of N-acetyl-, N-trifluoroacetyl-, N-mesyl-, and N-tosyldibenzothiophene sulfilimines

机译:N-乙酰基,N-三氟乙酰基,N-甲磺酰基和N-甲苯磺酰基二苯并噻吩硫亚胺的光化学

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摘要

Time-resolved infrared (TRIR) spectroscopy, product studies, and computational methods were applied to the photolysis of sulfilimines derived from dibenzothiophene that were expected to release acetylnitrene, trifluoroacetylnitrene, mesylnitrene, and tosylnitrene. All three methods provided results for acetylnitrene consistent with literature precedent and analogous experiments with the benzoylnitrene precursor, i.e., that the ground-state multiplicity is singlet. In contrast, product studies clearly indicate triplet reactivity for trifluoroacetylnitrene, though TRIR experiments were more ambiguous. Product studies suggest that these sulfilimines are superior sources for sulfonylnitrenes, which have triplet grounds states, to the corresponding azides, and computational studies shed light on the electronic structure of the nitrenes.
机译:时间分辨红外(TRIR)光谱学,产品研究和计算方法被应用于对二苯并噻吩衍生的亚硫亚胺的光解,这些亚硫胺有望释放出乙炔,三氟乙炔,甲磺腈和甲苯磺腈。所有这三种方法均提供了乙酰基氮化物的结果,该结果与文献中的先例和苯甲酰基氮化物前体的类似实验相一致,即基态多重性是单重态。相比之下,尽管TRIR实验更加模糊,但产品研究清楚地表明了三氟乙炔的三重态反应性。产品研究表明,这些亚磺胺是磺酰氮的优良来源,与相应的叠氮化物相比,它们具有三重基态,并且计算研究为腈的电子结构提供了线索。

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