The chemistry of zirconacycles and 2,6-diazasemibullvalenes : synthesis, structures, reactions, and applications in the synthesis of novel N-heterocycles /
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| Author / Creator: | Zhang, Shaoguang, author. |
|---|---|
| Imprint: | Heidelberg : Springer, [2015] |
| Description: | 1 online resource (xi, 173 pages) : illustrations (some color). |
| Language: | English |
| Series: | Springer Theses, 2190-5061 Springer theses. |
| Subject: | |
| Format: | E-Resource Book |
| URL for this record: | http://pi.lib.uchicago.edu/1001/cat/bib/11089416 |
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| 100 | 1 | |a Zhang, Shaoguang, |e author. |0 http://id.loc.gov/authorities/names/n2020007768 |1 http://viaf.org/viaf/916155284789087060214 | |
| 245 | 1 | 4 | |a The chemistry of zirconacycles and 2,6-diazasemibullvalenes : |b synthesis, structures, reactions, and applications in the synthesis of novel N-heterocycles / |c Shaoguang Zhang. |
| 264 | 1 | |a Heidelberg : |b Springer, |c [2015] | |
| 300 | |a 1 online resource (xi, 173 pages) : |b illustrations (some color). | ||
| 336 | |a text |b txt |2 rdacontent |0 http://id.loc.gov/vocabulary/contentTypes/txt | ||
| 337 | |a computer |b c |2 rdamedia |0 http://id.loc.gov/vocabulary/mediaTypes/c | ||
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| 490 | 1 | |a Springer Theses, |x 2190-5061 | |
| 588 | 0 | |a Online resource; title from PDF title page (SpringerLink, viewed December 19, 2014). | |
| 504 | |a Includes bibliographical references. | ||
| 500 | |a "Doctoral thesis accepted by Peking University, Beijing, China." | ||
| 505 | 0 | |a Introduction to Zirconacycle Chemistry -- Zirconocene-Mediated Cyclization of Bis(alkynyl)silanes and Nitriles: Synthesis of N-Heterocycles and Isolation, Characterization and Synthetic Application of Zr/Si-containing Reactive Intermediates -- Bulky-Nitrile Coordination Induced Skeleton Rearrangement of Zr/Si-containing Metallacycles and Selective Synthesis of 5-Azaindoles -- Introduction to Semibullvalenes and Azasemibullvalenes -- 2,6-Diazasemibullvalenes: Synthesis, Structure, Theoretical Analysis and Computational Chemistry -- 2,6-Diazasemibullvalenes: Reaction Chemistry and Synthetic Application. | |
| 520 | |a In this thesis, the author introduces two strategies used to construct various types of N-heterocycles, based on the chemistry of zirconacycles and 2,6-diazasemibullvalenes. In the first part, the author presents the development of multi-component cyclization of a zirconacyclobutene-silacyclobutene fused compound, nitriles and unsaturated compounds. These reactions provide synthetically useful methodology for various N-heterocycles such as 3-acyl pyrrole, pyrrolo[3,2-d]pyridazine and dihydropyrroloazepine, which are all difficult to synthesize by other means. The isolation and characterization of the key three-fused-ring Zr/Si-containing intermediates are also described in detail. These results show that the zirconacyclobutene-silacyclobutene fused compound behaves as a ℓ́ℓchemical transformerℓ́ℓ upon treatment with various substrates via the ℓ́ℓcoordination-induced skeleton rearrangementℓ́ℓ mechanism. In the second part, the author demonstrates the synthesis and isolation of a series of 2,6-diazasemibullvalenes (NSBVs) from the reaction of 1,4-dilithio-1,3-dienes and nitriles, highlighting the significant progress made for the first time in this work: (1) determination of X-ray crystal structure of a substituted 2,6-diazasemibullvalene; (2) measurement of the activation barrier of its rapid intramolecular aza-Cope rearrangement in solution; (3) exploration of several reaction types of NSBV with diverse ring-expansion products and ℓ́ℓbowl-shapeℓ́ℓ or ℓ́ℓcage-shapeℓ́ℓ N-containing polycyclic skeletons; (4) demonstration of the localized structure as the predominant form and the homoaromatic delocalized structure as a minor component in the equilibrium using theoretical analysis. Based on well-founded results, this work sheds new light on this controversial topic. | ||
| 650 | 0 | |a Organometallic compounds. |0 http://id.loc.gov/authorities/subjects/sh85095561 | |
| 650 | 4 | |a Metal complexes. | |
| 650 | 4 | |a Organometallic chemistry |x Research. | |
| 650 | 4 | |a Organometallic compounds. | |
| 650 | 4 | |a Polymers. | |
| 650 | 7 | |a SCIENCE |x Chemistry |x Organic. |2 bisacsh | |
| 650 | 7 | |a Organometallic compounds. |2 fast |0 (OCoLC)fst01047971 | |
| 655 | 4 | |a Electronic books. | |
| 776 | 0 | 8 | |i Printed edition: |z 9783662450208 |
| 830 | 0 | |a Springer theses. |0 http://id.loc.gov/authorities/names/no2010186160 | |
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