Journal ArticleDOI
En route towards α-benzotriazoyl nitroso derivatives
Jean-Christophe Monbaliu,Jean-Christophe Monbaliu,Lucas K. Beagle,Judit Kovacs,Matthias Zeller,Christian V. Stevens,Alan R. Katritzky,Alan R. Katritzky +7 more
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TLDR
In this paper, a new class of geminally-substituted nitroso compounds, i.e. α-benzotriazoyl derivatives, is presented.Abstract:
A new class of geminally-substituted nitroso compounds, i.e. α-benzotriazoyl nitroso derivatives, is presented. These compounds display a rather different behavior than other related nitroso compounds bearing a geminal electron-withdrawing group. An unexpected and spontaneous oxidation to the nitro analog is observed in solution.read more
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A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones
Victor-Emmanuel Kassin,Romain Morodo,Thomas Toupy,Isaline Jacquemin,Kristof Van Hecke,Raphaël Robiette,Jean-Christophe Monbaliu +6 more
TL;DR: This work showcases α-chloronitroso derivatives as economic and efficient vehicles for transferring electrophilic synthons of hydroxylamine toward nucleophilic enolates as well as a representative range of precursors and analogs of pharmaceutical active ingredients, including WHO essentials and drugs in shortage, according to a fully concatenated process.
Journal ArticleDOI
One pot conversion of benzophenone imine into the relevant 2-aza-allenium
Marco Bortoluzzi,Tiziana Funaioli,Fabio Marchetti,Guido Pampaloni,Calogero Pinzino,Stefano Zacchini +5 more
TL;DR: Interaction of common imines with WCl6 in organic solvents revealed very unusual features in the context of imine chemistry.
Book ChapterDOI
Preparation, Reactivity, and Synthetic Utility of Simple Benzotriazole Derivatives
TL;DR: The benzotriazole fragment is known to behave as an excellent leaving group, electron-donating or an electron-withdrawing group, an anion precursor, and a radical precursor as mentioned in this paper.
Journal ArticleDOI
On Demand Flow Platform for the Generation of Anhydrous Dinitrogen Trioxide and Its Further Use in <i>N</i> ‐Nitrosative Reactions
TL;DR: In this paper , an open-source setup and procedure for the on-demand generation of anhydrous N2 O3 solution (up to 1 M), which can be further used for reactions under batch and flow conditions.
Journal ArticleDOI
Three decades of unveiling the complex chemistry of <i>C</i>-nitroso species with computational chemistry
TL;DR: This paper revisited the complex reactivity of C -nitroso derivatives through the synergistic combination of computational and synthetic organic chemistry, with an emphasis on the rationalization of mechanisms and selectivities.
References
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Book
Density-functional theory of atoms and molecules
TL;DR: In this paper, a review of current studies in density functional theory and density matrix functional theory is presented, with special attention to the possible applications within chemistry, including the concept of an atom in a molecule, calculation of electronegativities from the Xα method, pressure, Gibbs-Duhem equation, Maxwell relations and stability conditions.
Journal ArticleDOI
Understanding the reactivity of captodative ethylenes in polar cycloaddition reactions. A theoretical study.
TL;DR: While the electrophilicity of the molecules accounts for the reactivity toward nucleophiles, it is shown that a simple index chosen for the nucleophilicity, Nu, based on the HOMO energy is useful explaining the reactsivity of these CD ethylenes toward electrophiles.
Journal ArticleDOI
Quantitative characterization of the global electrophilicity power of common diene/dienophile pairs in Diels–Alder reactions
TL;DR: The global electrophilicity power, ω, of a series of dienes and dienophiles commonly used in Diels-Alder reactions may be conveniently classified within a unique relative scale as discussed by the authors.
Journal ArticleDOI
A direct evaluation of regional Fukui functions in molecules
TL;DR: In this paper, a simple formalism to obtain regional Fukui functions is presented, which is based on an exact relationship between this local reactivity descriptor and the frontier molecular orbitals, and it becomes possible to define an orbital Fukui function that directly yields the condensed-to-atom quantity.