6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine can easily be prepared from aniline and paraformaldehyde. Its reactions with either N-bromosuccinimide (NBS) or with iodine monochloride (ICl) in the presence of a suitable activator smoothly afford 2-bromo- and 2-iodo- derivatives, respectively. The combination of these halogenation methods provides access to the 8-bromo-2-iodo derivative, which is an interesting and otherwise inaccessible intermediate for the synthesis of unsymmetrical analogs of Troger's base. The reported halogenations represent the first examples of electrophilic substitution in 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

中文翻译：

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6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine 的溴化和碘化：Tröger 碱不对称类似物的便捷入口

6H,12H-5,11-Methanodibenzo[b,f][1,5]diazocine 可以很容易地从苯胺和多聚甲醛制备。在合适的活化剂存在下，它与 N-溴代琥珀酰亚胺 (NBS) 或与一氯化碘 (ICl) 的反应分别顺利地得到 2-溴-和 2-碘-衍生物。这些卤化方法的组合提供了获得 8-bromo-2-iodo 衍生物的途径，这是一种有趣的中间体，用于合成 Troger 碱的不对称类似物。报道的卤化代表了 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine 亲电取代的第一个例子。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)