An unusual epimerization of a thioether

Woo Jin Chung, Ganga Viswanathan Bhagavathy, Neil E. Jacobsen, Stephanie Senef, Richard S. Glass

Research output: Contribution to journalArticlepeer-review


Reaction of 6-exo-methylthio-2-exo-phenylbicyclo[2.2.1]heptan-2-endo-ol with sodium azide and acid afforded the corresponding 2-exo-azide. This azide was reduced and acetylated to give a crystalline derivative whose structure was unequivocally established by X-ray crystallographic analysis. Surprisingly, the isomeric 6-endo-methylthio-2-exo-phenylbicyclo[2.2.1]heptan-2-endo-ol on reaction with sodium azide and acid yielded the same azide as the 6-exo-methylthio analogue. Evidence for the mechanism of thioisomerization is presented.

Original languageEnglish (US)
Pages (from-to)67-78
Number of pages12
JournalJournal of Sulfur Chemistry
Issue number1-2
StatePublished - Apr 1 2013


  • endo - exo rearrangement
  • norbornyl

ASJC Scopus subject areas

  • Chemistry(all)


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