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Tetrahedron | 1998

Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives

Mieczysław Ma̧kosza; Krzysztof Staliński

Abstract Tertiary carbanions generated from α-substituted phenylacetonitriles in liquid ammonia add to nitro-benzenes in the para position to form the corresponding σH-adducts which are transformed, depending on the starting nitriles and the reaction conditions, to products of oxidative nucleophilic substitution of hydrogen, ONSH or vicarious nucleophilic substitution, VNS.


Tetrahedron Letters | 1998

ISOTOPE EFFECT IN OXIDATIVE NUCLEOPHILIC SUBSTITUTION OF HYDROGEN IN NITROARENES

Mieczysław Mąkosza; Krzysztof Staliński

Abstract In a series of competitive experiments with labelled nitrobenzenes carried out in liquid ammonia at −70 °C it was shown that the rate of oxidative substitution of hydrogen with the carbanion of 2-phenylpropionitrile is ca . 9.8 times faster than the analogous substitution of deuterium in 4-D-nitrobenzene and perdeuterionitrobenzene. Thus C arom. -H bond breaking is the rate limiting step of the oxidative process.


Chemical Communications | 1996

Oxidative nucleophilic substitution of hydrogen in nitrobenzene with 2-phenylpropionitrile carbanion and potassium permanganate oxidant

Mieczysław Mąkosza; Krzysztof Staliński; Cezary Klępka

The carbanion of 2-phenylpropionitrile adds to nitrobenzene in the p-position in liquid ammonia to give the relative stable σH-adduct which is oxidised with KMnO4 to 2-phenyl-2-(4-nitrophenyl)propionitrile; the relationships of rates of various reactions in these systems are estimated.


Synlett | 2004

Application of the Radical Cascade of Acyclic Peptide-Based Precursors into Analogues of Type I β-Turn

Anita Stępień; Rafał Loska; Piotr Cmoch; Krzysztof Staliński

Radical cyclizations of di-, tri- and tetrapeptides containing N-2-bromobenzyl,N-methyl-substituted alanine or aspartic acid lead in good yields to α,β-unsaturated γ-lactams. The overall cascade, relying on a hydrogen atom transfer-elimination strategy could serve as a way to incorporate a flat and rigid five-membered ring into the peptide framework.


Chemistry: A European Journal | 1997

Oxidative Nucleophilic Substitution of Hydrogen in Nitroarenes

Mieczyslaw Makosza; Krzysztof Staliński


Journal of Organic Chemistry | 1998

DMD Oxidation of in-Situ-Generated σH Adducts Derived from Nitroarenes and the Carbanion of 2-Phenylpropionitrile to Phenols: The First Direct Substitution of a Nitro by a Hydroxy Group

Waldemar Adam; Mieczysław Ma̧kosza; Krzysztof Staliński; Cong Gui Zhao


Polish Journal of Chemistry | 1999

Oxidative Nucleophilic Substitution of Hydrogen in nitroarenes. A Short Review

Mieczysław Mąkosza; Krzysztof Staliński


Journal of Organometallic Chemistry | 2005

New distannanes containing the chiral 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand

Leszek Rupnicki; Zofia Urbanczyk-Lipkowska; Anita Stępień; Piotr Cmoch; Zbigniew Pianowski; Krzysztof Staliński


Journal of Molecular Structure | 2005

The 1H, 13C, 15N and 117Sn NMR study of the intramolecular Sn–N interaction in tri- and tetraorganotin compounds containing the chiral 2-(4-isopropyl-2-oxazolinyl)-5-phenyl ligand

Piotr Cmoch; Zofia Urbanczyk-Lipkowska; Armine Petrosyan; Anita Stępień; Krzysztof Staliński


Journal of Organic Chemistry | 2003

Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

Robert Andrukiewicz; Rafał Loska; Vladimir Prisyahnyuk; Krzysztof Staliński

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