180868-89-7Relevant academic research and scientific papers
Flash vacuum pyrolysis of azolylacroleins and azolylbutadienes
Lucero, Paola L.,Peláez, Walter J.,Riedl, Zsuzsanna,Hajós, Gy?rgy,Moyano, Elizabeth L.,Yranzo, Gloria I.
supporting information; experimental part, p. 1299 - 1305 (2012/02/13)
2-Aryl-5-acroleinyl-1,2,3,4-tetrazoles (1a-d) and 2-aryl-5-butadienyl-1,2, 3,4-tetrazoles (1e-g) were subjected to flash vacuum pyrolysis. Acroleinyl derivatives resulted in nitrogen extrusion to give nitrilimines followed by ring closure to give the corresponding indazoles 3a-d in good yields. On the other hand, butadiene derivatives underwent ring fragmentation to give p-substituted anilines without formation of the expected indazoles. Differences between thermal behaviour of 2-(4-chlorophenyl)-5-acroleinyl-1,2,3,4-tetrazole (1c) and 1-(4-chlorophenyl)-4-acroleinyl-1,2,3-triazole (2) were studied in details. DFT calculations have been used to examine the nitrilimine and carbene nature of the intermediates involved in the thermal reactions of azolyl derivatives.
