50741-91-8Relevant academic research and scientific papers
Transformations of arylcyclopropanes under the action of dinitrogen tetroxide
Mochalov,Kuz'min,Fedotov,Trofimova,Gazzaeva,Shabarov,Zefirov
, p. 1322 - 1330 (2007/10/03)
p-Bromophenylcyclopropane, 1- and 2-methylphenylcyclopropanes, and 1,2-di-p-tolyl- and l,2-bis(p-methoxyphenyl)cyclopropanes react with N2O4with opening of the three-membered ring. Reactions of p-methoxyphenylcyclopropane, 6-cyclopropyl-l,4-benzodioxane, and 2-cyclopropylfluorene yield the corresponding nitroaromatic derivatives with conservation of the cyclopropane ring. The nitration of p-methoxyphenylcyclopropane is accompanied by demethylation. 2-Nitro- and 4-nitrophenylcyclopropanes, as well as l-chloro-2-phenylcyclopropane, do not react with N2O4 under the same conditions. The differences in the behavior of arylcyclopropanes in reactions with N2O4 are explained by the different action of nitrosonium ion in the first reaction step: It acts as either electrophilic species capable of initiating opening of the cyclopropane ring or one-electron oxidant converting the initial arylcyclopropanes into the corresponding radical cations which are precursors of Wheland σ complexes responsible for aromatic nitration. copy;1998 MAHK "Hayka/Interperiodica".
BEHAVIOR OF 2-SUBSTITUTED 4-CYCLOPROPYLANISOLES DURING NITRATION WITH NITRIC ACID IN ACETIC ANHYDRIDE
Karpova, V. V.,Mochalov, S. S.,Shabarov, Yu. S.
, p. 268 - 277 (2007/10/02)
The nitration of 2-substituted 4-cyclopropylanisoles with 55 and 100percent nitric acid in acetic anhydride was studied.It was shown that the observed formal demethylation depends on the effect of the substituents on the realization of ipso attack and on
BEHAVIOR OF 2- AND 4-CYCLOPROPYLPHENYL ETHERS DURING NITRATION WITH NITRIC ACID IN ACETIC ANHYDRIDE
Mochalov, S. S.,Karpova, V. V.,Shabarov, Yu. S.
, p. 1780 - 1785 (2007/10/02)
During the nitration of 4-cyclopropyl phenyl ethers dilute nitric acid in acetic anhydride formal dealkylation (or dearylation) is realized with substituent entry of the nitro group into the para-substituted phenol which forms.Under analogous conditions the behavior of the corresponding ortho-substituted phenyl ethers depends both on the steric limitations created by the aroxyl (or alkoxyl) fragment and on its polar effect.In the reaction of cyclopropylphenyl ethers with concentrated nitric acid in acetic anhydride the formation of nitrophenols is hardly observed at all.
