70550-82-2Relevant articles and documents
Investigations on Diazo Compounds and Azides, XLIII. 1,2-Dewarpyridazines - Suitable Precursors for the Generation of Azacyclobutadienes?
Eisenbarth, Philipp,Regitz, Manfred
, p. 445 - 454 (2007/10/02)
Heating of the (diazomethyl)cyclopropenes 9b and c yields the pyridazines 10b and c as main products.The formation of the carbenes 11b and c, which decompose into the acetylenes 12 and 13, competes with the isomerization reaction.The pyridazine 10d is obtained immediately by electrophilic diazoalkane substitution of 6 with the cyclopropenylium salt 8; 9d can be established as intermediate by IR spectroscopy.The irradiation of the pyridazines 10a-d (10a is described in literature) leads to the stable 1,2-Dewarpyridazines 15a-d.The flash pyrolysis of 15b, conducted exemplarily, affords the fragment pairs 16 and 13b as well as 12 and 20.Their formation is in agreement with the intermediacy of the valence tautomeric azacyclobutadienes 1718.