74607-70-8Relevant academic research and scientific papers
Investigations on Diazo Compounds and Azides, XXXVI. - -Cycloaddition of Diazoalkanes to 1-Cyclopropenylphosphine Oxides; Isomerization of the Cyloadducts
Heydt, Heinrich,Busch, Karl-Heinz,Regitz, Manfred
, p. 590 - 599 (2007/10/02)
Reaction of the 1-cyclopropenyl(diphenyl)phosphine oxides 4a-d and the secondary diazoalkanes 5a-c affords the bicycles 6a-e in a regiospecific reaction.In an analogous way, the 1-pyrazolines 9a, c are obtained from 4b, d and diazomethane (8).In the case of the reaction 4c + 8 the regiospecifity is lost, with formation of the cycloadducts 9b and 10b.All diazomethane-adducts 9a-c and 10b isomerize to the 1,4-dihydropyridazines 11a-c and 12b when treated with ethanolic potassium hydroxide.The bicycles 6d, e and 9a, c may be transformed thermally into the allyl(phosphoryl)diazomethanes 13a-d, but only 13c and d could be isolated.
