Neighboring group participation in the additions of iodonium and bromonium ions to N-alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes (n = 1,2)

Grant R. Krow, Deepa Gandla, Weiwei Guo, Ryan A. Centafont, Guoliang Lin, Charles DeBrosse, Philip E. Sonnet, Charles W. Ross, Harri G. Ramjit, Patrick J. Carroll, Kevin C. Cannon

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

(Chemical Equation Presented) Additions of iodonium-X reagents to N-alkoxycarbonyl-2-azabicyclo[2.2.1]hept-5-enes and the homologous 2-azabicyclo[2.2.2]oct-5-enes have been found to mirror the outcomes of additions of bromonium-X reagents. Only rearranged products were observed for reactions of either of these halonium ion reagents with the azabicylo[2.2.1] hept-5-enes. For the azabicyclo[2.2.2]oct-5-enes, nitrogen participation in addition of IOH or BrOH was dependent on the N-alkoxycarbonyl group. With larger N-Boc, N-Cbz, or N-Troc protecting groups, unrearranged 5-anti-hydroxy-6-syn- I(or Br)-2-azabicyclo[2.2.2]octanes were formed by nucleophilic attack at C 5 on syn-halonium ions. The structure of N-methyl-8-anti-bromo-4- anti-hydroxy-2-azabicyclo[3.2.1]octane has been reassigned by X-ray analysis.

Original languageEnglish (US)
Pages (from-to)2114-2121
Number of pages8
JournalJournal of Organic Chemistry
Volume73
Issue number6
DOIs
StatePublished - Mar 21 2008

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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