Reactions of electrophilic chalcogenation (sulfenylation and selenenylation) of 7-azabicyclo[2.2.1]heptadiene derivatives with electron-withdrawing substituents at the nitrogen atom and the double bond were found to proceed trans-stereospecifically with the formation of 1,2-addition products, resulting from the exo-attack by the electrophile. In the case of 2-tosyl-7-azanorbornadiene, the reaction is regiospecific: the electrophilic species exclusively adds to the carbon atom at position 6. A comparative analysis of the behavior of dimethyl bicyclo-[2.2.1]heptadiene-2,3-dicarboxylate and its 7-aza analogs in the AdE reactions was carried out.

中文翻译：

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7-氮杂双环[2.2.1]庚二烯在亲电硫属化反应中的作用

发现 7-氮杂双环 [2.2.1] 庚二烯衍生物在氮原子和双键上具有吸电子取代基的亲电硫属化反应（磺基化和硒基化）反应以反式立体特异性进行，形成 1,2-加成产物，由亲电子试剂的外攻击引起。在 2-tosyl-7-azanorbornadiene 的情况下，反应是区域专一性的：亲电子物质只添加到 6 位的碳原子上。 二甲基双环-[2.2.1]heptadiene-2,3 行为的比较分析-二羧酸盐及其7-氮杂类似物在AdE反应中进行。