About: Diazonium Exchange and Migration of Pivaloyl Group upon Azo Coupling of -Enaminones

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	4,4-Dimethyl-1-methylamino-1-phenyl-2-(substituted phenyldiazenyl)pent-1-en-3-ones (prepared upon azo coupling of 4,4-dimethyl-1-methylamino-1-phenylpent-1-en-3-one 6a with the corresponding benzenediazonium tetrafluoroborates) react with another molecule of substituted benzenediazonium tetrafluoroborate (in dichloromethane in the presence of anhydrous sodium acetate) to form substituted 4,4-bis(substituted phenyldiazenyl) derivatives 8. The second azo coupling is reversible. Derivatives 8 undergo either reverse cleavage of a diazonium ion or [1,3] sigmatropic rearrangement forming substituted formazane 9. In the case of the sequential use of two different diazonium tetrafluoroborates, the less electrophilic group splits off more easily. The structures of the products 9 were studied by means of X-ray, H-1, C-13, F-19 and N-15 NMR and MALDI HRMS analyses. The formazans 9 exhibit a reduced mobility of the phenyl group adjacent to the pivaloyl group, giving rise to anisochronism of proton and carbon atoms, to eventually form conformers. The reduced mobility was observed by means of NMR spectroscopy. A temperature dependence of the spectral behaviour was also studied. 4,4-Dimethyl-1-methylamino-1-phenyl-2-(substituted phenyldiazenyl)pent-1-en-3-ones (prepared upon azo coupling of 4,4-dimethyl-1-methylamino-1-phenylpent-1-en-3-one 6a with the corresponding benzenediazonium tetrafluoroborates) react with another molecule of substituted benzenediazonium tetrafluoroborate (in dichloromethane in the presence of anhydrous sodium acetate) to form substituted 4,4-bis(substituted phenyldiazenyl) derivatives 8. The second azo coupling is reversible. Derivatives 8 undergo either reverse cleavage of a diazonium ion or [1,3] sigmatropic rearrangement forming substituted formazane 9. In the case of the sequential use of two different diazonium tetrafluoroborates, the less electrophilic group splits off more easily. The structures of the products 9 were studied by means of X-ray, H-1, C-13, F-19 and N-15 NMR and MALDI HRMS analyses. The formazans 9 exhibit a reduced mobility of the phenyl group adjacent to the pivaloyl group, giving rise to anisochronism of proton and carbon atoms, to eventually form conformers. The reduced mobility was observed by means of NMR spectroscopy. A temperature dependence of the spectral behaviour was also studied. (en)
Title	Diazonium Exchange and Migration of Pivaloyl Group upon Azo Coupling of -Enaminones Diazonium Exchange and Migration of Pivaloyl Group upon Azo Coupling of -Enaminones (en)
skos:prefLabel	Diazonium Exchange and Migration of Pivaloyl Group upon Azo Coupling of -Enaminones Diazonium Exchange and Migration of Pivaloyl Group upon Azo Coupling of -Enaminones (en)
skos:notation	RIV/00216275:25310/13:39896139!RIV14-MSM-25310___
http://linked.open...avai/predkladatel	Fakulta chemicko-technologická
http://linked.open...avai/riv/aktivita	I
http://linked.open...avai/riv/aktivity	I
http://linked.open...iv/cisloPeriodika	25
http://linked.open...vai/riv/dodaniDat	2014
http://linked.open...aciTvurceVysledku	Šimůnek, Petr Macháček, Vladimír
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Pardubice / Fakulta chemicko-technologická
http://linked.open...dnocenehoVysledku	69420
http://linked.open...ai/riv/idVysledku	RIV/00216275:25310/13:39896139
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Regioselectivity; Nitrogen heterocycles; Diazo compounds; Reaction mechanisms; Synthetic methods (en)
http://linked.open.../riv/klicoveSlovo	Regioselectivity Reaction mechanisms Diazo compounds Nitrogen heterocycles Synthetic methods
http://linked.open...odStatuVydavatele	DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV	[7D99EA445CEF]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	3 (xsd:int)
http://linked.open...UplatneniVysledku	2013
http://linked.open...v/svazekPeriodika	2013
http://linked.open...iv/tvurceVysledku	Šimůnek, Petr Macháček, Vladimír Bertolasi, Valerio
http://linked.open...ain/vavai/riv/wos	000323319500020
issn	1434-193X
number of pages	9 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201300534
http://localhost/t...ganizacniJednotka	25310

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