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首页> 外文期刊>Chemistry: A European journal >Reactivity of the 4-Amino-5H-1,2-Oxathiole-2,2-Dioxide Heterocyclic System: A Combined Experimental and Theoretical Study
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Reactivity of the 4-Amino-5H-1,2-Oxathiole-2,2-Dioxide Heterocyclic System: A Combined Experimental and Theoretical Study

机译：4-氨基-5H-1,2-氧硫醇-2,2-二氧化物杂环系统的反应性：组合的实验和理论研究

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摘要

The reactivity of the 4-amino-5H-1.2-oxathiole-2.2-dioxide (or beta-amino-gamma-sultone) heterocyclic system has scarcely been Studied. Here we describe the reactivity of this system towards electrophiles and airlines Oil readily available model substrates differently substituted at the C-5 position. A variety of C-electrophiles, carbonyl electrophiles (Such as acyl chlorides. isocyanates, or aldehydes) and halogen or nitrogen electrophiles have been explored. Both the C-3 and 4-amino positions of the beta-amino-gamma-sultone system are able to undergo electrophilic reactions, and the reaction products depend on the electrophile used and on the reaction conditions. On the other hand, nucleophilic attack of amines occurs at the C-4 position of the beta-amino-gamma-sultone system only in spiranic substrates hearing alicyclic substituents at the C-5 position. A comparative Computational study between spiranic and non-spiranic substrates suggests that conformational changes undergone on intermediate compounds. account for the observed reactivity differences. Moreover, these conformational changes seem to bring about an increase of electron density on the N-4 and C-3 atoms of the enaminic system, and a possible enhancement in the reactivity of spiranic substrates towards electrophiles in the presence of amines. Experimental data consistent with this predicted enhanced reactivity is also presented.
机译：几乎没有研究过4-氨基-5H-1.2-草硫醇-2.2-二氧化物（或β-氨基-γ-磺内酯）杂环系统的反应性。在这里，我们描述了该系统对亲电子试剂和航空公司的反应性。在C-5位置不同取代的石油易得的模型底物。已经研究了多种C亲电试剂，羰基亲电试剂（例如酰氯，异氰酸酯或醛）以及卤素或氮亲电试剂。 β-氨基-γ-磺内酯系统的C-3和4-氨基位置都能够进行亲电反应，反应产物取决于所用的亲电试剂和反应条件。另一方面，胺的亲核攻击仅在β-氨基-γ-磺内酯系统的C-4位置发生，仅在听到C-5位置有脂环族取代基的螺底物中。螺环和非螺环底物之间的比较计算研究表明，中间体化合物发生构象变化。解释了观察到的反应性差异。而且，这些构象变化似乎导致烯胺体系的N-4和C-3原子上的电子密度增加，并且在存在胺的情况下螺环底物对亲电试剂的反应性可能增强。还提供了与此预测的增强的反应性一致的实验数据。

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