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Off the Beaten Path: Almost Clean Formation of Indene from the ortho-Benzyne + Allyl Reaction.

ABSTRACT: 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.

SUBMITTER: McCabe MN

PROVIDER: S-EPMC7168585 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Off the Beaten Path: Almost Clean Formation of Indene from the <i>ortho</i>-Benzyne + Allyl Reaction.

McCabe Morgan N MN Hemberger Patrick P Reusch Engelbert E Bodi Andras A Bouwman Jordy J

The journal of physical chemistry letters 20200327 8

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 <i>o</i>-benzyne. Here we report on a combi ...[more]

PMID: 32202794

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