Rearrangement of methylenecamphor during electrophilic bromination: Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

Allen A. Thomas, Keith A. Monk, Sonia Abraham, Stella Lee, Charles M. Garner

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominated (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemistry confirmed by both polarimetric and chiral GC analyses. Two transformations of the product were also performed to elucidate the structure.

Original languageEnglish (US)
Pages (from-to)2261-2263
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number12
DOIs
StatePublished - Mar 18 2001
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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