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Cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene: A Convenient Enediyne
Organic Letters ( IF 4.9 ) Pub Date : 2021-08-24 , DOI: 10.1021/acs.orglett.1c02459 Annadka Shrinidhi 1 , Charles L Perrin 1
Organic Letters ( IF 4.9 ) Pub Date : 2021-08-24 , DOI: 10.1021/acs.orglett.1c02459 Annadka Shrinidhi 1 , Charles L Perrin 1
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Enediynes are widely studied to understand their cycloaromatization and the trapping of the resulting p-dehydrobenzene diradical. However, few model substrates are known, and they are hard to synthesize and difficult to handle. Herein we report cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene as a convenient model for studying the reactivity of enediynes. It can be easily synthesized from 1,2-diethynylcyclohexene and 1,4-diiodobutane. It is a solid that is stable at room temperature. In solution the p-dehydrobenzene diradical derived from its cycloaromatization can be trapped by nucleophiles. The rate-limiting step is the cyclization, which is slightly slower than that of the parent cyclodec-1,5-diyne-3-ene but faster than that of its benzo analogue, consistent with the distances between the reacting carbon atoms.
中文翻译：
Cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene：一种方便的烯二炔
烯二炔被广泛研究以了解它们的环芳构化和所得对脱氢苯双自由基的捕获。然而，已知的模型基板很少，并且它们难以合成且难以处理。在此，我们报告了 cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene 作为研究烯二炔反应性的便捷模型。它可以很容易地由 1,2-二乙炔基环己烯和 1,4-二碘丁烷合成。它是一种在室温下稳定的固体。在溶液中p由其环芳构化衍生的-脱氢苯双自由基可以被亲核试剂捕获。限速步骤是环化，它比母体 cyclodec-1,5-diyne-3-ene 稍慢，但比其苯并类似物快，与反应碳原子之间的距离一致。
更新日期：2021-09-03
中文翻译：
Cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene：一种方便的烯二炔
烯二炔被广泛研究以了解它们的环芳构化和所得对脱氢苯双自由基的捕获。然而，已知的模型基板很少，并且它们难以合成且难以处理。在此，我们报告了 cyclohexeno[3,4]cyclodec-1,5-diyne-3-ene 作为研究烯二炔反应性的便捷模型。它可以很容易地由 1,2-二乙炔基环己烯和 1,4-二碘丁烷合成。它是一种在室温下稳定的固体。在溶液中p由其环芳构化衍生的-脱氢苯双自由基可以被亲核试剂捕获。限速步骤是环化，它比母体 cyclodec-1,5-diyne-3-ene 稍慢，但比其苯并类似物快，与反应碳原子之间的距离一致。
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