Ring expansion/homologation-aldehyde condensation cascade using tert-trihalomethylcarbinols

J. R. Falck, Anyu He, L. Manmohan Reddy, Abhijit Kundu, Deb K. Barma, A. Bandyopadhyay, Sukanta Kamila, Radha Akella, Romain Bejot, Charles Mioskowski

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Treatment of cyclic tert-trihalomethylcarbinols with CrCl2 in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.

Original languageEnglish (US)
Pages (from-to)4645-4647
Number of pages3
JournalOrganic Letters
Volume8
Issue number20
DOIs
StatePublished - Sep 28 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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