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首页> 外文期刊>Chemistry: A European journal >N, N'-Bis (2, 2-dimethylpropyl) benzimidazolin-2-ylidene: A Stable Nucleophilic Carbene Derived from Benzimidazole
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N, N'-Bis (2, 2-dimethylpropyl) benzimidazolin-2-ylidene: A Stable Nucleophilic Carbene Derived from Benzimidazole

机译：N，N'-双（2，2-二甲基丙基）苯并咪唑啉-2-亚烷基：稳定的苯并咪唑亲核化碳烯

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摘要

N, N'-Dialkylated benzimidazol-2-thiones 6 can be prepared in a three-step procedure from o-phenylenediamine. Thione 6a was reduced with sodium/potassium under desulfurization leading to carbene 4. Compound 4 is the first stable free carbene derived from benzimidazole. It exhibits the topology of an unsaturated carbene including a short C4-C5 bond. Its ~(13)C NMR spectrum [#delta#(C2) = 231.47] and selected structural parameters [angle N1-C2-N3 103.5(1) deg and 104.2 (1) deg], however, correspond to those of saturated carbenes of the imidazolidin-2-ylidene type 3. The observation that the unsaturated carbene 4 behaves like a saturated imidazolidin-2-ylidene is corroborated by the tendency of the sterically less bulky N, N'-dialkylated thione 6b to yield the olefin 8 after reduction with Na/K. Carbene 4 can be coordinated to a W (CO)_5 fragment yielding the complex 9, which contains a nonplanar carbene ring.
机译：N，N′-二烷基化苯并咪唑-2-硫酮6可以由邻苯二胺按三步法制备。在脱硫条件下，用钠/钾将亚硫酰6a还原生成卡宾4。化合物4是第一个稳定的衍生自苯并咪唑的游离卡宾。它表现出具有短C4-C5键的不饱和卡宾的拓扑结构。它的〜（13）C NMR光谱[＃delta＃（C2）= 231.47]和选定的结构参数[N1-C2-N3角103.5（1）度和104.2（1）度），对应于饱和卡宾N，N′-二烷基化硫酮6b在空间上体积较小的趋势，在不饱和卡宾4的行为类似于饱和的咪唑烷基-2-亚烷基的观察结果上得到证实。用Na / K还原。卡宾4可以配位为W（CO）_5片段，生成含有非平面卡宾环的配合物9。

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