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Statements

Subject Item
n2:RIV%2F60461373%3A22310%2F08%3A00020041%21RIV09-MSM-22310___
rdf:type
n9:Vysledek skos:Concept
dcterms:description
Aminokarbenové komplexy chromu nesoucí methylovou skupinu v o-poloze aromatického kruhu byly rozštěpeny na enentiomery. Aminocarbene complexes having a methyl group in the o-position to the aminocarbene moiety on the aromatic ring, (S)-pentacarbonyl[(N,N-dimethylamino)-(3-methoxycarbonyl-2-methylphenyl)carbene]chromium(0) [(S)-6] and (R)-pentacarbonyl[(N,N-dimethylamino)-(5-methoxycarbonyl-2-methylphenyl)carbene]chromium(0) [(R)-7] were prepared in enantiomerically pure form by the crystallization of diastereoisomeric esters with (S)-1-(1-naphthyl)ethanol. In the case of (S)-6 the racemization barrier DG?rac=(121 ? 0.5) kJxmol-1 was established. The substitution of o-methyl group with isopropyl group did not virtually change the racemization barrier (DG?rac= (120.5 ? 0.5) kJxmol-1), while the introduction of o-phenyl group led to substantial lowering of DG?rac. Attempts to transfer chirality in thermal reactions of the complexes (S)-6 and (R)-7 with alkynes, palladium-catalyzed insertion into C-H bond and photochemical formation of b-lactams were unsuccessful. Aminocarbene complexes having a methyl group in the o-position to the aminocarbene moiety on the aromatic ring, (S)-pentacarbonyl[(N,N-dimethylamino)-(3-methoxycarbonyl-2-methylphenyl)carbene]chromium(0) [(S)-6] and (R)-pentacarbonyl[(N,N-dimethylamino)-(5-methoxycarbonyl-2-methylphenyl)carbene]chromium(0) [(R)-7] were prepared in enantiomerically pure form by the crystallization of diastereoisomeric esters with (S)-1-(1-naphthyl)ethanol. In the case of (S)-6 the racemization barrier DG?rac=(121 ? 0.5) kJxmol-1 was established. The substitution of o-methyl group with isopropyl group did not virtually change the racemization barrier (DG?rac= (120.5 ? 0.5) kJxmol-1), while the introduction of o-phenyl group led to substantial lowering of DG?rac. Attempts to transfer chirality in thermal reactions of the complexes (S)-6 and (R)-7 with alkynes, palladium-catalyzed insertion into C-H bond and photochemical formation of b-lactams were unsuccessful.
dcterms:title
Enantiomerically Pure Axially Chiral Aminocarbene Complexes of Chromium Enantiomerně čisté axiálně chirální aminokarbenové komplexy chromu Enantiomerically Pure Axially Chiral Aminocarbene Complexes of Chromium
skos:prefLabel
Enantiomerically Pure Axially Chiral Aminocarbene Complexes of Chromium Enantiomerně čisté axiálně chirální aminokarbenové komplexy chromu Enantiomerically Pure Axially Chiral Aminocarbene Complexes of Chromium
skos:notation
RIV/60461373:22310/08:00020041!RIV09-MSM-22310___
n4:aktivita
n14:P n14:Z
n4:aktivity
P(GA203/00/1240), P(GA203/04/0487), Z(MSM0021620857), Z(MSM6046137301)
n4:cisloPeriodika
8
n4:dodaniDat
n7:2009
n4:domaciTvurceVysledku
n5:3295303 n5:5078008 n5:8605580
n4:druhVysledku
n15:J
n4:duvernostUdaju
n18:S
n4:entitaPredkladatele
n17:predkladatel
n4:idSjednocenehoVysledku
366119
n4:idVysledku
RIV/60461373:22310/08:00020041
n4:jazykVysledku
n12:eng
n4:klicovaSlova
aminokarbene complexes of chromium; axial chirality; enantiomers
n4:klicoveSlovo
n6:enantiomers n6:axial%20chirality n6:aminokarbene%20complexes%20of%20chromium
n4:kodStatuVydavatele
US - Spojené státy americké
n4:kontrolniKodProRIV
[92D48DEFF86C]
n4:nazevZdroje
Organometallics
n4:obor
n19:CC
n4:pocetDomacichTvurcuVysledku
3
n4:pocetTvurcuVysledku
4
n4:projekt
n10:GA203%2F00%2F1240 n10:GA203%2F04%2F0487
n4:rokUplatneniVysledku
n7:2008
n4:svazekPeriodika
27
n4:tvurceVysledku
Drahoňovský, Dušan Meca, Luděk Dvořák, Dalimil Císařová, Ivana
n4:wos
000254981000026
n4:zamer
n16:MSM6046137301 n16:MSM0021620857
s:issn
0276-7333
s:numberOfPages
9
n13:organizacniJednotka
22310