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 Citations (Scopus)

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

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Heptanes
Stereochemistry
Halogenation
X ray crystallography
X Ray Crystallography
pyridine
2-methylenecamphor

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Rearrangement of methylenecamphor during electrophilic bromination : Remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system. / Thomas, Allen A.; Monk, Keith A.; Abraham, Sonia; Lee, Stella; Garner, Charles M.

In: Tetrahedron Letters, Vol. 42, No. 12, 18.03.2001, p. 2261-2263.

Research output: Contribution to journalArticle

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