184302-79-2Relevant articles and documents
Study of the Features of the Reaction of Arylcyclopropanes with Nitrozonium Ethyl Sulfate or Nitrozonium Tetrafluoroborate
Bondarenko, O. B.,Gavrilova, A. Yu.,Solodovnikova, T. A.,Tikhanushkina, V. N.,Zyk, N. V.
, p. 753 - 762 (2020/07/03)
Abstract: The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF4 were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopropane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products formed with the participation of an external nucleophile are formed.
PhIO promoted synthesis of nitrile imines and nitrile oxides within a micellar core in aqueous media: A regiocontrolled approach to synthesizing densely functionalized pyrazole and isoxazoline derivatives
Pal, Gargi,Paul, Sanjay,Ghosh, Partha Pratim,Das, Asish R.
, p. 8300 - 8307 (2014/02/14)
A highly efficient and general protocol has been developed for the facile synthesis of highly diversified 1,3,5-trisubstituted pyrazoles and 3,5-disubstituted 2-isoxazolines through one-pot tandem intermolecular, as well as intramolecular, dipolar [3 + 2] cycloaddition reactions. Chemoselective oxidation of aldohydrazone to nitrile imine and aldoximes to nitrile oxides by iodosobenzene in neutral aqueous media was performed. The scope of the reactions in regiocontrolled dipolar cycloaddition with olefins in the presence of PhIO toward highly substituted pyrazole and isoxazoline derivatives has been demonstrated. SDS converted the initially floating reaction mass and the organo-oxidant PhIO into a homogeneous mixture, which on stirring became a turbid emulsion. The micellar arrangement was confirmed by dynamic light scattering and optical microscopy. The new, green and metal free synthetic method enabled the execution of regiocontrolled tandem cycloaddition oxidation sequences leading to a library of pyrazole and isoxazoline derivatives.
New aspects of nitrosation of arylcyclopropanes: Nitrosation of phenylcyclopropanes with bulky alkyl substituents in the small ring
Bondarenko,Gavrilova,Saginova,Zyk,Zefirov
experimental part, p. 1275 - 1283 (2009/06/05)
It has been shown for the first time that nitrosation of phenylcyclopropanes with bulky alkyl substituents in the small ring proceeds predominantly with attack of the nitrosonium cation on the benzyl carbon atom of the cyclopropane ring with intermediate
