| Current
Organic Chemistry
ISSN: 1385-2728
Current Organic
Chemistry
Volume 9, Number 1, January 2005
Contents
Asymmetric Ring Opening of Epoxides Pp.1-29
I. M. Pastor and M. Yus
[Abstract]
[Full text article]
Selective Catalytic Oxidations in Supercritical
Carbon Dioxide Pp.31-47
Sandro Campestrini and Umberto Tonellato
[Abstract]
[Full text article]
Novel Regioselective Preparation of 5-Chloropyrazine-2-Carbonitrile
from Pyrazine-2-Carboxamide and Coupling Study of Substituted
Phenylsulfanylpyrazine-2-Carboxylic Acid Derivatives Pp.49-60
Josef Jampilek, Martin Dolezal, Jiri Kunes, Dalibor Satinsky
and Ivan Raich
[Abstract] [Full
text article]
Physical Organic Perspectives on Phospho Group
Transfer From Phosphates and Phosphinates Pp.61-74
A.C. Hengge and I. Onyido
[Abstract] [Full
text article]
Chlorine Isotope Effects on Chemical Reactions
Pp.75-88
D. Sicinska, M. Rostkowski and P. Paneth
[Abstract] [Full
text article]
Abstracts
[Back to top]
Asymmetric Ring Opening of Epoxides
I. M. Pastor and M. Yus
[Full text article]
This review deals with the metal promoted asymmetric ring
opening of achiral epoxides using achiral carbon-, nitrogen-,
oxygen-, sulphur- and halogen-containing nucleophiles. The
use of chiral bases in the asymmetric deprotonation of achiral
epoxides yields chiral allylic alcohols. Finally, kinetic
resolution of racemic epoxides can be achieved using chiral
metal complexes.
[Back to top]
Selective Catalytic Oxidations in Supercritical Carbon
Dioxide
Sandro Campestrini and Umberto Tonellato
[Full text
article]
Supercritical carbon dioxide is ideally suited as reaction
medium for catalytic oxidations of organic substrates, and
it may be exploited as one of the most promising strategies
to realize some fundamental chemical transformations under
environmentally benign conditions. The use of supercritical
carbon dioxide as solvent for unselective hydrocarbons auto-oxidations
is extensively described in the literature. Conversely, only
a limited number of reports deal with selective oxidations
carried out by molecular oxygen or by other primary oxidants
such as hydrogen peroxide, alkyl hydroperoxides, monopersulfate,
etc. In this paper recent developments in selective catalytic
oxidations are reviewed and particular attention is devoted
to those processes in which a metal derivative, capable of
selectively oxidizing various substrates, is formed by action
of a terminal oxidant such as oxygen or an organic or inorganic
peroxide.
[Back to top]
Novel Regioselective Preparation of 5-Chloropyrazine-2-Carbonitrile
from Pyrazine-2-Carboxamide and Coupling Study of Substituted
Phenylsulfanylpyrazine-2-Carboxylic Acid Derivatives
Josef Jampilek, Martin Dolezal, Jiri Kunes, Dalibor
Satinsky and Ivan Raich
[Full text
article]
A new method of 5-chloropyrazine-2-carbonitrile preparation
in a regioselective fashion and the study of the coupling
of the pyrazine ring with variously substituted benzenethiols
are described. A radical-ionic mechanism of this coupling,
carried out in the presence of a heterogeneous copper catalyst,
has been proposed. The reactivity of the substituted chloropyrazines
is correlated to the calculated values of electronic deficiency
in positions C(6) or C(5) or C(3) of the pyrazine ring. This
nucleophilic substitution provided a series of substituted
phenylsulfanylpyrazine-2- carboxylic acid derivatives. The
synthetic approach, analytical and spectroscopic data of all
compounds are presented.
[Back to top]
Physical Organic Perspectives on Phospho Group Transfer From
Phosphates and Phosphinates
A.C. Hengge and I. Onyido
[Full text
article]
As phosphoryl transfer reactions are ubiquitous in biological
chemistry, organic chemists have been very interested in the
mechanisms of phosphate and phosphinate esters. Physical organic
chemistry methods, including stereochemical studies, linear
free energy relationships, and, most recently, heavy-atom
kinetic isotope effects, have been used in the quest for mechanistic
information about the chemistry of these compounds. This review
summarizes what has been learned about the uncatalyzed phosphoryl
transfer reactions of phosphate and phosphinate esters.
[Back to top]
Chlorine Isotope Effects on Chemical Reactions
D. Sicinska, M. Rostkowski and P. Paneth
[Full text
article]
A critical review of applications of chlorine kinetic isotope
effects in studies of organic reactions mechanisms is presented.
Reports from the last five years are considered. During this
time chlorine kinetic isotope effects were applied mainly
in studies of elimination reactions and nucleophilic substitution
reactions. In several cases chemical models were also used
as models of the intrinsic kinetic isotope effects in several
enzymatic reactions. Both experimental and theoretical approaches
have been used.
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