Relative migratory aptitudes of hydrogen, benzoyl, 4-methoxyphenyl and 4-nitrophenyl groups in some unsaturated carbenes (vinylidenes)

Ferenc Bertha, József Fetter, Károly Lempert, Mária Kajtár-Peredy, Gábor Czira, Erno Koltai

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

([5-13C] Tetrazol-5-yl)methyl ketones were prepared and subjected to oxidative fragmentation induced by lead tetraacetate. The resulting intermediate [1-13C]-3-oxoprop-1-en-1-ylidenes rearrange, depending on the relative migratory aptitudes of the benzoyl group and the ligands R, either to [3-13C]prop-2-yn-1-ones or to [2-13C]prop-2-yn-1-ones or to mixtures of the two isomers. The 1H and/or 13C NMR spectra of the products allow the three cases to be distinguished. The relative migratory aptitudes were found to be H>PhCO, 4-MeOC6H4>4-O2NC6H 4.

Original languageEnglish
Pages (from-to)8889-8895
Number of pages7
JournalTetrahedron
Volume57
Issue number42
DOIs
Publication statusPublished - Oct 15 2001

Keywords

  • Benzoyl vinylidenes
  • C labelling
  • Carbenes
  • Migratory aptitudes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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