40791-03-5Relevant articles and documents
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
EFFECT OF THE NATURE OF SUBSTITUENTS IN THE THREE-CARBON RING ON THE DEMETHYLATION OF p-CYCLOPROPYLANISOLES DURING NITRATION
Mochalov, S. S.,Karpova, V. V.,Shabarov, Yu. S.
, p. 495 - 503 (2007/10/02)
The behavior of a series of p-cyclopropylanisoles substituted in the small ring was investigated under conditions favoring their demethylation during nitration.It was shown that the yields of the nitrophenols which form depend on the nature and on the pos
