111479-61-9Relevant articles and documents
1,3-Dipolar Cycloaddition Reactions of Nitrilium Betaines with Aryl Thiocyanates and Selenocyanates
Greig, Derek J.,Hamilton, Douglas G.,McPherson, Michael,Paton, R. Michael,Crosby, John
, p. 607 - 612 (2007/10/02)
The carbon-nitrogen triple bond of aryl thiocyanates acts as a dipolarophile in 1,3-dipolar cycloadditions.Reaction with nitrile oxides, nitrile sulphides, and benzonitrile N-phenylimide yields, respectively, 5-arylthio-1,2,4-oxadiazoles, -thidiazoles and -triazoles.Aryl selenocyanates behave similarly forming 5-arylseleno-1,2,4-oxadiazoles and -thiadiazoles from nitrile oxides and sulphides.Divergent pathways are followed by the reactions of secondary amines such as piperidine with 5-arylthio-1,2,4-oxadiazoles and -thidiazoles, the former yielding 5-piperidyl-1,2,4-oxadiazoles and the latter dihydro-1,2,4-thiadiazole-5-thiones.