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

Vyacheslav V Diev; Oksana N Stetsenko; Tran Q Tung; Jürgen Kopf; Rafael R Kostikov; Alexander P Molchanov

doi:10.1021/jo702379d

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

J Org Chem. 2008 Mar 21;73(6):2396-9. doi: 10.1021/jo702379d. Epub 2008 Feb 28.

Authors

Vyacheslav V Diev¹, Oksana N Stetsenko, Tran Q Tung, Jürgen Kopf, Rafael R Kostikov, Alexander P Molchanov

Affiliation

¹ Department of Chemistry, St. Petersburg State University, 198504 Universitetsky pr. 26, St. Petersburg, Russian Federation.

PMID: 18303913
DOI: 10.1021/jo702379d

Abstract

1,3-Dipolar cycloaddition of C-aryl,N-aryl (or N-methyl) nitrones with a number of 1,2-diphenylcyclopropenes substituted at the C(3) position occurs with the formation of expected "normal" cycloadducts (with N-methylnitrones) and products of their subsequent transformations. Among them are corresponding alpha-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 C(3( position of cyclopropenes by an electron acceptor group decreases the reactivity of cyclopropenes.