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首页> 外文期刊>Chemistry: A European journal >Bromination of unsaturated dodecahedranes - En route toC(20) fullerene
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Bromination of unsaturated dodecahedranes - En route toC(20) fullerene

机译：不饱和十二面体的溴化-通往C（20）富勒烯的途中

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摘要

As part of a study to achieve selective oligo(poly)bromination-ultimately perbromination-of the dodecahedral C-20 skeleton, the extent and direction of the ionic bromination of dodecahedrene and 1,16-dodecahedradiene were explored. Along sequences of Br+ additions/deprotonations and allylic rearrangements, up to ten hydrogen atoms were substituted (traces of C20HxBr10). Tetrabromododecahedrenes obtained under defined conditions in up to 50% total yield with three and four allylic bromine substituents protecting the extremely bent C=C bonds, proved highly unreactive even towards oxygen but reacted rapidly with CH2N2. Upon electron impact ionization (MS) of the newly secured oligo(poly)bromododecahedra(e)nes, sequential loss of the substituents ended generally in polyunsaturated dodecahedranes (in the extreme C20H4, "tetrahydro-C-20 fullerenes"). Only subsequently did skeletal fragmentations occur. From X-ray crystal-structure analyses, more information was obtained on the structural response of the dodecahedral skeleton to the strain induced by the voluminous substituents. As Appendix, the forcing radical bromination of 1,6-dibromododecahedrane and exploratory cis-beta-HBr/cis-p-Br-2 eliminations in bromododecahedranes with [Fe-2(CO)(9)], P2F/[FeCP2] and [Fe(tmeda)Cp*Cl] (in situ protection) are presented.
机译：作为实现十二面体C-20骨架的选择性低聚（最终）全溴化的研究的一部分，研究了十二碳烯和1,16-十二碳烯的离子溴化的程度和方向。沿着Br +加成/去质子化和烯丙基重排的顺序，最多取代了10个氢原子（C20HxBr10的痕迹）。在限定条件下以高达50％的总收率得到的四溴十二碳烯，具有三个和四个烯丙基溴取代基保护极度弯曲的C = C键，甚至对氧也没有反应性，但与CH2N2迅速反应。在新固定的低聚（聚）溴二十二碳六烯（e）酮进行电子碰撞电离（MS）时，取代基的顺序损失通常以多不饱和十二面体为代表（在极端C20H4中为“四氢-C-20富勒烯”）。仅随后发生骨骼碎裂。通过X射线晶体结构分析，获得了有关十二面体骨架对由大量取代基诱导的应变的结构响应的更多信息。作为附录，用[Fe-2（CO）（9）]，P2F / [FeCP2]和[Fe-2（CO）（3）]强制溴化十二碳二十烷中的1,6-二溴二十二碳六烯进行自由基溴化和顺式β-HBr/ cis-p-Br-2的探索性消除。提出了[Fe（tmeda）Cp * Cl]（原位保护）。

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