The Synthesis of some 4‐Nitroisoxazoles from Pseudonitrosites of Chalcones
The action of dinitrogen trioxide with α,β‐unsaturated ketones of the chalcone type leads to pseudonitrosites (Table 1) which are cyclized to 4‐nitro‐3,5‐diarylisoxazoles (Table 2).
197. Les pseudonitrosites en chimie organosilicique par Henri Jollbois, Andre Doucet ct Roger .Perrot laboratoire de Chimie G6nBrale Facult6 des Scicnccs -32, rue Mkgevancl, 1; -25030. Hcsanpn (28. 11.74) Summccvy. The reaction 01 dinitrogcn trioxide with sevcn hilanes containing an ethylcIii(: chain, lead to pseudonitrositcs.
Cette étude a conduit aux conclusions suivantes:
Par action due cyanogène sur le lithium, en présence de fer, on parvient à des mélanges de cyanure et de cyanamide accompagnés de paracyanogène.
L'action de l'acide cyanhydrique gezeux sur la lithine, en absence de fer, conduit à des mélanges contenant des quantités de paracyanogène.
Nitric oxide reacts with phenylethylene and arylalkenes under the action of sunlight and at room temperature giving dimeric nitronitroso compounds prouved by IR. spectroscopy (see Table 2) and the corresponding nitroolefins. The main gaseous product is nitrogen as prouved by gaz liquid chromatography (see Table 1). The dimeric nitronitroso compounds can also be obtained by the reaction of dinitrogen trioxide with olefins. The structure of the nitronitroso compounds was further discussed. They may be reduced to give monoamines corresponding to the nitrogroup and may be also converted into nitroolefins.
Nitrosyl chloride is only chlorinating in darkness and above 100°. In the sun light and at room temperature it reacts as a chlorinating, nitrosating, nitrating and oxidizing agent. With trichlorethylene in fact pentachlorethane 1,1,1,2‐tetrachloro‐2‐nitrosoethane, 1,1,1,2‐tetrachloro‐2‐nitroethane, dichloracetic acid and a compound of empirical formula C4H2Cl5NO2 are obtained. Tetrachloroethylene carried to hexachlorethane, pentachloronitrosoethane and tetrachloro‐2‐(pentachlorethyl)‐1,2‐oxazetidine.
Introduced nitrosyl chloride provided nitrogen monoxide prouved by gaz chromatography. This monoxide reacted afterwards to give nitrogen which is the single nitrogenous gazeous compound. Carbondioxide is a minor component of the gaz.
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