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SYNTHESIS OF 1-NITROPENTACHLORO-1,3-BUTADIENE AND ITS REACTIONS WITH O- AND N-NUCLEOPHILIC AND BIFUNCTIONAL NUCLEOPHILIC REAGENTS
Potkin, V. I.,Kaberdin, R. V.,Oldekop, Yu. A.
, p. 48 - 54 (2007/10/02)
The previously unknown 1-nitropentachloro-1-butadiene was obtained by the action of 57-68percent nitric acid on cis-1-H-pentachloro-1,3-butadiene at 70-75 deg C.The reaction of nitrodiene with sodium alcoholates takes place with substitution of the nitro group and leads to a 3:1 mixture of the cis and trans isomers of the respective 1-alkoxy-1,2,3,4,4-pentachloro-1,3-butadienes.The action of primary and secondary amines and also of monoethanolamine on the nitrodiene leads to substitution of the chlorine atom at the second carbon atom of the diene system and the formationof 1-nitro-2-amino-1,3,4,4-tetrachloro-1,3-butadienes.The reaction of the nitrodiene with ethylenediamine takes place with substitution of the chlorine atoms in two molecules of the nitrodiene and leads to N,N'-bis(1-nitro-1,3,4,4-tetrachloro-1,3-butadienyl)ethylenediamine.It was established that the amino derivatives of the nitrodiene are formed as a single isomer
