Pinacol rearrangement of jojoba bis-epoxide

Inna Zeltser, Arnon Shani

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Jojoba bis-epoxide (1.6 mmol) undergoes pinacol rearrangement upon reaction with the iodide ion (60 mmol) under slightly acidic conditions, via an iodohydrin as an intermediate, to yield bis-ketojojoba in high yield (92%) after 25 h reflux in THF; no hydroxy derivatives were detected. Since the nucleo-philic opening of the epoxide ring is statistically equal on both sides, the rearranged product may have the two carbonyl groups on either side of the original carbon atoms of the two epoxide rings, both completely opened. MS of the rearranged products reveals that the ring opening is approximately equal on both sides of the epoxide ring. Other nucleophiles, such as acetate and amine, open the ring sluggishly without rearrangement.

Original languageEnglish
Pages (from-to)597-601
Number of pages5
JournalJAOCS, Journal of the American Oil Chemists' Society
Volume79
Issue number6
DOIs
StatePublished - 1 Jan 2002

Keywords

  • Epoxide
  • Jojoba wax
  • Mass spectra
  • Pinacol rearrangement

ASJC Scopus subject areas

  • General Chemical Engineering
  • Organic Chemistry

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