Application of [hydroxy(tosyloxy)iodo]benzene in the wittig-ring expansion sequence for the synthesis of β-benzocycloalkenones from α-benzocycloalkenones

Michael W. Justik, Gerald F. Koser

Research output: Contribution to journalArticle

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Abstract

The conversion of α-benzocycloalkenones to homologous β-benzocycloalkenones containing six, seven and eight-membered rings is reported. This was accomplished via a Wittig olefination-oxidative rearrangement sequence using [hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis of regioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation of carbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIB approach is a useful alternative to analogous sequences in which Tl(NO3) 3·3H2O or the Prevost combination (AgNO 3/I2) are employed in the oxidation step.

Original languageEnglish (US)
Pages (from-to)217-225
Number of pages9
JournalMolecules
Volume10
Issue number1
DOIs
Publication statusPublished - Jan 2005

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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