Chemische Berichte, volume 116, issue 10, pages 3427-3437
Photochemische Stickstoff‐Eliminierung aus 1‐Alkenyl‐4‐alkyl‐1,4‐dihydro‐5 H ‐tetrazol‐5‐onen und ‐thionen. Diaziridinone und Carbodiimide mit Alkenylsubstituenten
Publication type: Journal Article
Publication date: 1983-10-01
Inorganic Chemistry
Abstract
Um zu prufen, ob aus Tetrazolonen und Tetrazolthionen durch photochemische Stickstoff-Eliminierung Zwischenstufen entstehen, die sich durch intramolekulare [3 + 2]-Cycloaddition an CC-Doppelbindungen abfangen lassen, wurden einige Tetrazolone 8 und -thione 13 mit Alkenylsubstituenten dargestellt und photolysiert. Mit Licht von λ = 254 nm erhielt man aus den Tetrazolonen 8 in [D3]Acetonitrile, [D12]Cyclohexan und [D14]Methylcyclohexan Stickstoff und 80–90% Diaziridinone 17 neben geringen Mengen Nebenprodukten (< 10%), die sich in [D3]Acetonitril als Photoreduktionsprodukt, Harnstoff 18, und als Hydrolyseprodukt von 17 erwiesen. Die Thione 13 eliminierten beim Belichten Stickstoff und Schwefel und gaben Carbodiimide. In keinem Fall beobachtete man intramolekulare [3 + 2]-Cycloaddition einer Zwischenstufe.
Photoextrusion of Nitrogen from 1-Alkenyl-4-alkyl-1,4-dihydro-5H-tetrazol-5-ones and -thiones. Diaziridinones and Carbodiimides with Alkeyl Substituents
To test the possibility that tetrazolones and tetrazolthiones photoextrude nitrogen producing intermediates which can be trapped via intramolecular [3 + 2]-cycloaddition to CC double bonds, several tetrazolones 8 and -thiones 13 with alkenyl substituents were synthesized and subjected to photolysis. On 254 nm photolysis of the tetrazolones 8 in [D3]acetonitrile, [D12]cyclohexane, and [D14]methylcyclohexane as solvents, nitrogen was extruded and diaziridinones 17 were formed in 80–90% yield besides small amounts of by-products (< 10%). When the photolysis was carried out in [D3]acetonitrile, the latter were identified as urea 18 (photoreduction product) and as the hydrolysis product of 17. The thiones 13 photoextruded nitrogen and sulfur producing carbodiimides. Trapping of an intermediate via [3 + 2]-cycloaddition was not observed.
Top-30
Citations by journals
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Chemische Berichte
4 publications, 14.81%
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3 publications, 11.11%
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Journal of Organic Chemistry
2 publications, 7.41%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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1 publication, 3.7%
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Citations by publishers
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10
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Wiley
10 publications, 37.04%
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Elsevier
4 publications, 14.81%
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American Chemical Society (ACS)
4 publications, 14.81%
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Pleiades Publishing
4 publications, 14.81%
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Springer Nature
2 publications, 7.41%
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Multidisciplinary Digital Publishing Institute (MDPI)
1 publication, 3.7%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 3.7%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Quast H., Nahr U. Photochemische Stickstoff‐Eliminierung aus 1‐Alkenyl‐4‐alkyl‐1,4‐dihydro‐5 H ‐tetrazol‐5‐onen und ‐thionen. Diaziridinone und Carbodiimide mit Alkenylsubstituenten // Chemische Berichte. 1983. Vol. 116. No. 10. pp. 3427-3437.
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Quast H., Nahr U. Photochemische Stickstoff‐Eliminierung aus 1‐Alkenyl‐4‐alkyl‐1,4‐dihydro‐5 H ‐tetrazol‐5‐onen und ‐thionen. Diaziridinone und Carbodiimide mit Alkenylsubstituenten // Chemische Berichte. 1983. Vol. 116. No. 10. pp. 3427-3437.
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TY - JOUR
DO - 10.1002/cber.19831161017
UR - https://doi.org/10.1002/cber.19831161017
TI - Photochemische Stickstoff‐Eliminierung aus 1‐Alkenyl‐4‐alkyl‐1,4‐dihydro‐5 H ‐tetrazol‐5‐onen und ‐thionen. Diaziridinone und Carbodiimide mit Alkenylsubstituenten
T2 - Chemische Berichte
AU - Quast, Helmut
AU - Nahr, Uwe
PY - 1983
DA - 1983/10/01 00:00:00
PB - Wiley
SP - 3427-3437
IS - 10
VL - 116
SN - 0009-2940
ER -
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@article{1983_Quast,
author = {Helmut Quast and Uwe Nahr},
title = {Photochemische Stickstoff‐Eliminierung aus 1‐Alkenyl‐4‐alkyl‐1,4‐dihydro‐5 H ‐tetrazol‐5‐onen und ‐thionen. Diaziridinone und Carbodiimide mit Alkenylsubstituenten},
journal = {Chemische Berichte},
year = {1983},
volume = {116},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/cber.19831161017},
number = {10},
pages = {3427--3437},
doi = {10.1002/cber.19831161017}
}
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Quast, Helmut, and Uwe Nahr. “Photochemische Stickstoff‐Eliminierung aus 1‐Alkenyl‐4‐alkyl‐1,4‐dihydro‐5 H ‐tetrazol‐5‐onen und ‐thionen. Diaziridinone und Carbodiimide mit Alkenylsubstituenten.” Chemische Berichte, vol. 116, no. 10, Oct. 1983, pp. 3427-3437. https://doi.org/10.1002/cber.19831161017.