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Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings

School of Chemistry, University College Dublin, D04 V1W8 Belfield, Dublin 4, Ireland
Academic Editors: Teresa Pinho e Melo and Maria Isabel L. Soares
Molecules 2020, 25(20), 4730; https://doi.org/10.3390/molecules25204730
Received: 23 September 2020 / Revised: 13 October 2020 / Accepted: 14 October 2020 / Published: 15 October 2020
(This article belongs to the Special Issue Diels-Alder Reaction in Organic Synthesis)
The intermediacy of short-lived isoindenes, generated in the course of metallotropic or silatropic shifts over the indene skeleton, can be shown by Diels-Alder trapping with tetracyanoethylene, leading to the complete elucidation of the dynamic behaviour of a series of polyindenylsilanes. Cyclopentadienones, bearing ferrocenyl and multiple phenyl or naphthyl substituents undergo [4 + 2] cycloadditions with diaryl acetylenes or triphenylcyclopropene to form the corresponding polyarylbenzenes or cycloheptatrienes. The heptaphenyltropylium cation, [C7Ph7+], was shown to adopt a nonplanar shallow boat conformation. In contrast, the attempted Diels-Alder reaction of tetracyclone and phenethynylfluorene yielded electroluminescent tetracenes. Finally, benzyne addition to 9-(2-indenyl)anthracene, and subsequent incorporation of a range of organometallic fragments, led to development of an organometallic molecular brake. View Full-Text
Keywords: isoindenes; tetracyanoethylene; ferrocenylhexaphenylcycloheptatriene; tropylium ions; hexanaphthylbenzene; X-ray crystallography; organometallic molecular brake isoindenes; tetracyanoethylene; ferrocenylhexaphenylcycloheptatriene; tropylium ions; hexanaphthylbenzene; X-ray crystallography; organometallic molecular brake
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MDPI and ACS Style

McGlinchey, M.J. Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings. Molecules 2020, 25, 4730. https://doi.org/10.3390/molecules25204730

AMA Style

McGlinchey MJ. Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings. Molecules. 2020; 25(20):4730. https://doi.org/10.3390/molecules25204730

Chicago/Turabian Style

McGlinchey, Michael J. 2020. "Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings" Molecules 25, no. 20: 4730. https://doi.org/10.3390/molecules25204730

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