Off the Beaten Path: Almost Clean Formation of Indene from the ortho-Benzyne + Allyl Reaction.,The Journal of Physical Chemistry Letters

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Off the Beaten Path: Almost Clean Formation of Indene from the ortho-Benzyne + Allyl Reaction.
The Journal of Physical Chemistry Letters ( IF 4.8 ) Pub Date : 2020-03-27 , DOI: 10.1021/acs.jpclett.0c00374
Morgan N McCabe ₁ , Patrick Hemberger ₂ , Engelbert Reusch ₃ , Andras Bodi ₂ , Jordy Bouwman ₁

Affiliation

Polycyclic aromatic hydrocarbons (PAHs) play an important role in chemistry both in the terrestrial setting and in the interstellar medium. Various, albeit often inefficient, chemical mechanisms have been proposed to explain PAH formation, but few yield polycyclic hydrocarbons cleanly. Alternative and quite promising pathways have been suggested to address these shortcomings with key starting reactants including resonance stabilized radicals (RSRs) and o-benzyne. Here we report on a combined experimental and theoretical study of the reaction allyl + o-benzyne. Indene was found to be the primary product and statistical modeling predicts only 0.1% phenylallene and 0.1% 3-phenyl-1-propyne as side products. The quantitative and likely barrierless formation of indene yields important insights into the role resonance stabilized radicals play in the formation of polycyclic hydrocarbons.

中文翻译：

走出人迹罕至的地方：邻位苯甲酸+烯丙基反应几乎可以干净地形成茚。

多环芳烃（PAHs）在地面环境和星际介质中在化学中都起着重要作用。已经提出了各种尽管通常效率低下的化学机理来解释PAH的形成，但是很少能干净地产生多环烃。已经提出了替代的且非常有希望的途径来解决关键的起始反应物，包括共振稳定的自由基（RSR）和邻苯并ne，以解决这些缺点。在这里，我们报告了对烯丙基+邻-苄基反应的综合实验和理论研究。发现茚是主要产物，统计模型预测只有0.1％的苯丙二烯和0.1％的3-苯基-1-丙炔是副产物。

更新日期：2020-04-24

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