87243-57-0Relevant academic research and scientific papers
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.
Δ2-isoxazolines from arylcyclopropanes: III. Phenylcyclopropanes substituted in three-membered ring in reaction with nitrosyl chloride activated with oxides of sulfur(IV, VI)
Bondarenko,Gavrilova,Saginova,Zyk,Zefirov
experimental part, p. 218 - 225 (2009/09/25)
The reaction of phenylcyclopropanes substituted in the three-membered ring with nitrosyl chloride activated with sulfur(IV, VI) oxides provided in good yield substituted 5-phenylisoxazolines as a mixture of structural isomers.
Insertion of Nitrogen Oxide and Nitrosonium Ion into the Cyclopropane Ring: A New Route to 2-Isoxazolines and its Mechanistic Studies
Mizuno, Kazuhiko,Ichinose, Nobuyuki,Tamai, Toshiyuki,Otsuji, Yoshio
, p. 4669 - 4675 (2007/10/02)
The 9,10-dicyanoanthracene (DCA)-sensitized photoreaction of 1,2-diarylcyclopropanes 1a-d in nitrogen oxide (NO)-saturated CH3CN afforded 3,5-diaryl-2-isoxazolines 2a-d in excellent yields.The reaction of 1a-d with NOBF4 or with a mixture of NO and O2 in
SYNTHESIS OF ISOXAZOLINES FROM ARYLCYCLOPROPANES UNDER NITROSATION CONDITIONS
Shabarov, Yu. S.,Saginova, L. G.,Gazzaeva, R. A.
, p. 589 - 593 (2007/10/02)
It is shown that the corresponding isoxazolines are formed in high yields when aryl-, diaryl-, and alkylarylcyclopropanes are treated with sodium nitrite in trifluoroacetic or trichloroacetic acid at 0 deg C.The reaction does not take place in acetic or c
