X=Y-ZH Systems as potential 1,3-dipoles. Part 51: Halogen-induced inter- and intra-molecular formation of nitrones from oximes and alkenes

DÖNDAŞ H. A., Grigg R., Hadjisoteriou M., Markandu J., Kennewell P., Thornton-Pett M.

TETRAHEDRON, vol.57, no.6, pp.1119-1128, 2001 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 57 Issue: 6
  • Publication Date: 2001
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1119-1128
  • Keywords: oximes, hetereoatom nucleophiles, dimeric nitrone salts cycloaddition, MEDIATED HETEROATOM CYCLIZATIONS, C PI-BONDS, ISOXAZOLIDINE CASCADES, CYCLIC NITRONES
  • Çukurova University Affiliated: No

Abstract

Grimes possessing gamma- and delta -alkenyl substituents are cyclised by N-bromo- or N-iodosuccinimide, iodine or IC1 to the corresponding cyclic nitrones or their dimeric H-bonded hydroiodide salts in good yield; facially specific cycloaddition of these nitrones, and others derived by cyclisation of delta,delta -bis(alkenyl) ketoximes or by iodine induced addition of acetaldoxime to cyclohexene, furnish isoxazolidines. (C) 2001 Elsevier Science Ltd. All rights reserved.