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Description
  • A new reaction mechanism for the Lossen rearrangement of hydroxamic acids catalyzed by basic salts is presented. It is shown that the rearrangement proceeds in metal complexes of deprotonated hydroxamic acids. The deprotonation can occur either at the oxygen atom (observed for the zinc complexes) or at the nitrogen atom (observed for the potassium complexes). Both anionic forms are characterized by infrared multiphoton dissociation spectroscopy. The rearrangements proceed from the reactive N-deprotonated metal hydroxamates and lead to metal carbamates. The mechanism is elucidated by computational chemistry, mass-spectrometric studies, and preparative experiments.
  • A new reaction mechanism for the Lossen rearrangement of hydroxamic acids catalyzed by basic salts is presented. It is shown that the rearrangement proceeds in metal complexes of deprotonated hydroxamic acids. The deprotonation can occur either at the oxygen atom (observed for the zinc complexes) or at the nitrogen atom (observed for the potassium complexes). Both anionic forms are characterized by infrared multiphoton dissociation spectroscopy. The rearrangements proceed from the reactive N-deprotonated metal hydroxamates and lead to metal carbamates. The mechanism is elucidated by computational chemistry, mass-spectrometric studies, and preparative experiments. (en)
Title
  • Metal-assisted Lossen Rearrangement
  • Metal-assisted Lossen Rearrangement (en)
skos:prefLabel
  • Metal-assisted Lossen Rearrangement
  • Metal-assisted Lossen Rearrangement (en)
skos:notation
  • RIV/00216208:11310/12:10128764!RIV13-GA0-11310___
http://linked.open...avai/predkladatel
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • I, P(GAP207/11/0338), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika
  • 6
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
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  • 149639
http://linked.open...ai/riv/idVysledku
  • RIV/00216208:11310/12:10128764
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • chemistry; reactivity; density; dissociation; zinc-complexes; histone deacetylase; infrared-spectroscopy; hydroxamic acids; gas-phase; ionization mass-spectrometry (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [043B5FD72925]
http://linked.open...i/riv/nazevZdroje
  • Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor
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http://linked.open...vavai/riv/projekt
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http://linked.open...v/svazekPeriodika
  • 77
http://linked.open...iv/tvurceVysledku
  • Roithová, Jana
  • Hanikýřová, Eva
  • Jašíková, Lucie
  • Jašík, Juraj
  • Škríba, Anton
http://linked.open...ain/vavai/riv/wos
  • 000301516100024
http://linked.open...n/vavai/riv/zamer
issn
  • 0022-3263
number of pages
http://bibframe.org/vocab/doi
  • 10.1021/jo300031f
http://localhost/t...ganizacniJednotka
  • 11310
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