ChemInform Abstract: Para‐Alkylsubstituted Phenylcyclopropanes in the Reaction with Dinitrogen Tetroxide.

Abstract

078ChemInform Abstract The reaction between N2O4 (II) and phenylcyclopropane (Ia) and its p-alkylsubstituted derivatives (Ib) proceeds at -30 rc C regiospecifically at the cyclopropyl moiety. The formed adducts are stable only at low temperature. On warming to room temperature they decompose to give mixtures of the benzaldehydes (III), the cinnamic aldehydes (IV) and the 5-arylisoxazolines (V). The formation of the primary adducts and of the products (III)-(V) is discussed.

Reaction of Halogenated Cyclopropanes and Nitrosyl Cation: Preparation of Isoxazoles

“…In this study, we found that 2,2-dichlorobicyclo[4.1.0]heptane ( 17 ) can undergo a similar reaction to give alkyl-substituted isoxazoles 33 . It is important to note that this is in contrast to previous reports that have stated that only the cyclopropyl rings which contain an aryl group are subjected to opening and the formation of isoxazolines or isoxazoles. −

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“…We can now prepare the isoxazoles by the reaction of dihalogenocyclopropane and nitrosyl cation, taking advantage of the halogen as a leaving group (Scheme ). In contrast to previous reports that cyclopropanes must contain aryl groups for rearrangement, − these isoxazoles were formed by the reaction of nitrosyl cation with either the arylcyclopropanes or alkylcyclopropanes.

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“…Isoxazoles are typically prepared by the reaction of nitrile oxides with alkynes or by cyclization of the adducts of α,β-unsaturated ketones (or aldehydes) and hydroxylamines . More recently, isoxazolines have been prepared by the nitrosation of cyclopropanes using a mixture of sodium nitrite and trifluoroacetic acid, dinitrogen tetraoxide, cupric nitrate in acetic anhydride, and nitrosyl cation in acetonitrile …”

Oxidative Coupling of Benzenes with α,β-Unsaturated Aldehydes by the Pd(OAc)2/Molybdovanadophosphoric Acid/O2 System

“…The products 18 and 20 were converted into the corresponding carboxylic acids 18 ‘ and 20 ‘ during the isolation process. 4 , 6 , p - 8 , 10 , 12 , 14 , 16 , 17 , m - 18 , 20 , 22 , 23 , and 24a 17 are known compounds and have been reported previously. 3 , m - and p - 10 , p - 18 , p - 18 ‘, p - 20 , p - 20 ‘, and 24b are commercially available.…”

Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

“…One of the paths for the production of heterocyclic compounds is direct single-stage synthesis from arylcyclopropanes [287][288][289][290][291][292][293][294][295][296]. Thus, one of the promising trends in the synthesis of nitrogen-and oxygen-containing heterocyclic compounds, which was first identified in the Laboratory of Organic Synthesis at the Department of Organic Chemistry (Yu.…”