Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings
Abstract
:1. Introduction
2. Diels-Alder Trapping of Isoindenes
2.1. Metallotropic Shifts
2.2. Silatropic Shifts
3. Diels-Alder Cycloadditions of Alkynes or Triphenylcyclopropene to Cyclopentadienones
3.1. Geometric Factors in CnPhn Ring Systems
3.2. Syntheses and Structures of Heptaarylcycloheptatrienes
3.3. The Heptaphenyltropylium Cation
3.4. Boron and Nitrogen Analogues of Heptaphenylcycloheptatrienes
3.5. Ferrocenyl-Substituted Polyaryl-Benzenes and -Cycloheptatrienes
3.6. Hexa(β-naphthyl)benzene and Ferrocenyl-penta(β-naphthyl)benzene
3.7. Other Organometallic Derivatives of C6Ph6 and C7Ph7H
3.8. Organometallic Derivatives of Persubstituted Cycloheptatrienes
3.8.1. Octachlorocycloheptatriene, C7Cl8
3.8.2. The heptamethyltropylium Cation, [C7Me7+]
3.8.3. Heptacarbomethoxycycloheptatriene, C7(CO2Me)7H
4. Diels-Alder Cycloadditions en Route to Organometallic Molecular Brakes
4.1. Attempted Preparation of Fluorenyl-Pentaphenylbenzene
4.2. Successful Route to a Molecular Brake via Addition of Benzyne to 9-(2-Indenyl)anthracene
5. Diels-Alder Cycloadditions with Subsequent Molecular Rearrangement
6. Concluding Remarks
Funding
Acknowledgments
Conflicts of Interest
References
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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
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 StyleMcGlinchey, 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