Nitrone cycloadditions to 1,2-diphenylcyclopropenes and subsequent transformations of the isoxazolidine cycloadducts

Article abstract of DOI:10.1021/jo702379d

(Chemical Equation Presented) 1,3-Dipolar cycloaddition of C-aryl,N-aryl (or N-methyl) nitrones with a number of 1,2-diphenylcyclopropenes substituted at the C³ position occurs with the formation of expected "normal" cycloadducts (with N-methylnitrones) and products of their subsequent transformations. Among them are corresponding α-acetophenyl aziridines and tetra (or penta) -arylpyrroles. Aziridines and the normal cycloadducts can be also thermally converted to such arylpyrroles with moderate to good yields. Substitution at the C³ position of cyclopropenes by an electron acceptor group decreases the reactivity of cyclopropenes.