Chemische Berichte, volume 118, issue 2, pages 526-540
Photochemische Stickstoff‐Eliminierung aus 1,4‐Dihydro‐1‐phenyl‐5 H ‐tetrazol‐5‐onen und ‐thionen. Benzimidazolone und Carbodiimide
Publication type: Journal Article
Publication date: 1985-02-01
Inorganic Chemistry
Abstract
Die nachtragliche Einfuhrung einer Phenylgruppe an N-4 des Tetrazolrings gelingt erstmals, namlich durch Alkylierung des 1-Phenyltetrazolons 10a mit 2-Cyclohexen-1-ylbromid zu 10f und anschliesende Dehydrierung mit 2,3-Dichlor-5,6-dicyan-1,4-benzochinon zu 10 g. Die photochemische Stickstoff-Eliminierung aus 1-Phenyltetrazolonen, unsubstituiert (10a) oder mit einer Methyl- (10 b), Propenyl- (10d,e) oder Phenylgruppe (10 g) an N-4, ergibt nahezu quantitativ die entsprechenden Benzimidazolone 14a,b,d,e,g. Durch Bestrahlung der 1-Phenyltetrazolthione 8b, f, g erhalt man neben Stickstoff und Schwefel die Carbodiimide 22b, f, g, wahrend aus 8a Phenylcyanamid (25) entsteht. Im Gegensatz zur bekannten Thermolyse, die zu 2-(Methylamino)-benzothiazol (21b) fuhrt, ergibt die Photolyse des (Phenylimino)-1,2,3,4-thiatriazols 24, ein Isomeres des Methylphenyltetrazolthions 8b, ebenfalls Stickstoff, Schwefel und Methylphenyl-carbodiimid (22b).
Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides
Alkylation of 1-phenyltetrazolone 10a with 2-cyclohexen-1-yl bromide followed by dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone permits introduction of a phenyl group at N-4 of the tetrazole ring via the sequence 10a 10f 10g. The photoextrusion of molecular nitrogen from the (N-4)-substituted 1-phenyltetrazolones, 10a (hydrogen), 10b (methyl), 10d,e (propenyl), and 10g (phenyl) produces essentially quantitative yields of the corresponding benzimidazolones 14a,b,d,e,g. On irradiation of the 1-phenyltetrazolethiones 8 b, f, g the carbodiimides 22b, f, g are obtained together with molecular nitrogen and sulfur, while 8a affords phenylcyanamide (25). In contrast to the thermolysis, which is known to give 2-(methylamino)benzothiazole (21 b), photolysis of the (phenylimino)-1,2,3,4-thiatriazole 24, an isomer of methylphenyltetrazolethione 8b, also yields molecular nitrogen, sulfur, and methylphenylcarbodiimide (22b).
Top-30
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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1 publication, 2.56%
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Citations by publishers
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Elsevier
9 publications, 23.08%
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Wiley
9 publications, 23.08%
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American Chemical Society (ACS)
5 publications, 12.82%
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Multidisciplinary Digital Publishing Institute (MDPI)
2 publications, 5.13%
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Springer Nature
2 publications, 5.13%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
2 publications, 5.13%
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Royal Society of Chemistry (RSC)
2 publications, 5.13%
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Pleiades Publishing
2 publications, 5.13%
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Taylor & Francis
1 publication, 2.56%
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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 1,4‐Dihydro‐1‐phenyl‐5 H ‐tetrazol‐5‐onen und ‐thionen. Benzimidazolone und Carbodiimide // Chemische Berichte. 1985. Vol. 118. No. 2. pp. 526-540.
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Quast H., Nahr U. Photochemische Stickstoff‐Eliminierung aus 1,4‐Dihydro‐1‐phenyl‐5 H ‐tetrazol‐5‐onen und ‐thionen. Benzimidazolone und Carbodiimide // Chemische Berichte. 1985. Vol. 118. No. 2. pp. 526-540.
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TY - JOUR
DO - 10.1002/cber.19851180213
UR - https://doi.org/10.1002/cber.19851180213
TI - Photochemische Stickstoff‐Eliminierung aus 1,4‐Dihydro‐1‐phenyl‐5 H ‐tetrazol‐5‐onen und ‐thionen. Benzimidazolone und Carbodiimide
T2 - Chemische Berichte
AU - Quast, Helmut
AU - Nahr, Uwe
PY - 1985
DA - 1985/02/01 00:00:00
PB - Wiley
SP - 526-540
IS - 2
VL - 118
SN - 0009-2940
ER -
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@article{1985_Quast,
author = {Helmut Quast and Uwe Nahr},
title = {Photochemische Stickstoff‐Eliminierung aus 1,4‐Dihydro‐1‐phenyl‐5 H ‐tetrazol‐5‐onen und ‐thionen. Benzimidazolone und Carbodiimide},
journal = {Chemische Berichte},
year = {1985},
volume = {118},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/cber.19851180213},
number = {2},
pages = {526--540},
doi = {10.1002/cber.19851180213}
}
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Quast, Helmut, and Uwe Nahr. “Photochemische Stickstoff‐Eliminierung aus 1,4‐Dihydro‐1‐phenyl‐5 H ‐tetrazol‐5‐onen und ‐thionen. Benzimidazolone und Carbodiimide.” Chemische Berichte, vol. 118, no. 2, Feb. 1985, pp. 526-540. https://doi.org/10.1002/cber.19851180213.