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Keywords = benzyne cycloadditions

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27 pages, 14624 KiB  
Review
The Effect of Benzannulation on the Structures, Reactivity and Molecular Dynamics of Indenes, Pentalenes, Azulenes and Related Molecules
by Michael J. McGlinchey
Molecules 2022, 27(12), 3882; https://doi.org/10.3390/molecules27123882 - 17 Jun 2022
Cited by 2 | Viewed by 2140
Abstract
The stabilising effect of benzannulation on isoindenes formed in the course of sigmatropic shifts of (C5H5)Fe(CO)2 or of organo-silyl groups, and on exocyclic allyl intermediates in the course of haptotropic shifts of organometallic fragments over polycyclic skeletons (fluorene, [...] Read more.
The stabilising effect of benzannulation on isoindenes formed in the course of sigmatropic shifts of (C5H5)Fe(CO)2 or of organo-silyl groups, and on exocyclic allyl intermediates in the course of haptotropic shifts of organometallic fragments over polycyclic skeletons (fluorene, cyclopenta[def]phenanthrene, syn and anti dibenzpentalenes) is exemplified. This approach led to the development of the first organometallic molecular brake. Benzyne cycloadditions to anthracenes to form triptycenes also led to unexpected or multiple adducts that were characterised by X-ray crystallography. Synthetic routes to the previously elusive benz[cd]azulene system are presented. Finally, the complete mechanism of the stepwise assembly of dispiro- and diindenyltetracenes from fluorenylallenes is presented, whereby every intermediate has been unambiguously structurally characterised. Full article
(This article belongs to the Special Issue Benzannulations in Organic Synthesis)
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26 pages, 10508 KiB  
Review
Diels-Alder Additions as Mechanistic Probes–Interception of Silyl-Isoindenes: Organometallic Derivatives of Polyphenylated Cycloheptatrienes and Related Seven-Membered Rings
by Michael J. McGlinchey
Molecules 2020, 25(20), 4730; https://doi.org/10.3390/molecules25204730 - 15 Oct 2020
Cited by 3 | Viewed by 3541
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Diels-Alder Reaction in Organic Synthesis)
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5 pages, 49 KiB  
Short Note
One-pot Microwave-Assisted Synthesis of 1H-Phenanthro[9,10- d][1,2,3]triazole
by Avat Arman Taherpour and Mehrak Faraji
Molbank 2008, 2008(3), M577; https://doi.org/10.3390/M577 - 4 Sep 2008
Cited by 5 | Viewed by 5122
Abstract
In this study, a fast and good yield one-pot microwave-assisted synthesis (45 seconds) of 1H-phenanthro[9,10-d][1,2,3]triazole by a 1,3-dipolar cycloaddition reaction of sodium azide and 9-bromophenanthrene in the presence of potassium tert-butoxide in DMSO as solvent is reported. Full article
9 pages, 55 KiB  
Article
7-(1-Acetoxymethylidene)Benzonorbornadiene: A Versatile Reagent for the Synthesis of 7-Formyl and 7-Hydroxymethyl Benzonorbornadienes
by Ronald N. Warrener, Geoffrey J. Collin and Patrick J. Foley
Molecules 2001, 6(3), 194-202; https://doi.org/10.3390/60300194 - 28 Feb 2001
Cited by 4 | Viewed by 6957
Abstract
7-(1-Acetoxymethylidene)benzonorbornadiene 3, prepared in one step by the addition of benzyne to 6-acetoxyfulvene 2, is hydrolysed in acid solution to form a 3:2-epimeric mixture of syn- and anti- 7-formylbenzonorbornadienes 4 and 5, respectively; the corresponding 7-hydroxymethylbenzonorbornadienes 6 and 9 were produced by reduction [...] Read more.
7-(1-Acetoxymethylidene)benzonorbornadiene 3, prepared in one step by the addition of benzyne to 6-acetoxyfulvene 2, is hydrolysed in acid solution to form a 3:2-epimeric mixture of syn- and anti- 7-formylbenzonorbornadienes 4 and 5, respectively; the corresponding 7-hydroxymethylbenzonorbornadienes 6 and 9 were produced by reduction of the formyl isomers with sodium borohydride. Full article
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