87839-61-0Relevant articles and documents
1,3-Dipolar Cycloadditions, 87. Contributions to the Chemistry of N-Phenylnitrilimine
Huisgen, Rolf,Fliege, Werner,Kolbeck, Winfried
, p. 3027 - 3038 (2007/10/02)
The N-phenyl derivative 7 is introduced as the first monosubstituted and interceptible nitrilimine whereas the cycloadditions of disubstituted representatives have been preparatively utilized in the past.Photolysis of 2-phenyltetrazole in the presence of methyl acrylate gives rise to methyl 1-phenyl-2-pyrazoline-5-carboxylate which on further irradiation suffers ring cleavage.The sodium salt of α-nitroformaldehyde phenylhydrazone (15) eliminates NaNO2 in refluxing acetonitrile whereby the intermediate 7 is accepted in situ by acrylic ester, styrene and norbornene.The interaction of methyl acrylate with the anionic precursor 15 furnishes further products.The formal dimer of 7, the 1,4-diphenyl-1,4-dihydro-1,2,4,5-tetrazine, is probably formed by reaction of 7 with 15.