Abstract

The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF₄ were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopropane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products formed with the participation of an external nucleophile are formed.

中文翻译：

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芳基环丙烷与硫酸氮氮唑鎓或四氟硼酸氮氮鎓反应的特性研究

摘要

在三氧化硫和三氧化硫二恶烷络合物存在下，二芳基，芳基和烷基芳基环丙烷与亚硝酸乙酯的反应，以及1-烷基-2-芳基环丙烷与NOBF _4的反应被研究了。已发现，亚硝基阳离子的侵蚀伴随着苄基碳阳离子的形成导致异恶唑啉的形成。将大量的烷基取代基引入环丙烷环中会改变亚硝化的区域选择性，有利于亲电粒子在苄基位置上的进攻，并导致形成烷基碳阳离子的竞争性形成。取决于烷基取代基的结构，形成了伴随骨架重排的分子内杂环化产物和在外部亲核试剂参与下形成的产物。