The gas-phase elimination reaction of 3-methoxycyclohexene: regiochemistry

John J. Rabasco, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

12 Scopus citations


Gas-phase elimination reactions of deuterium labeled 3-methoxycyclohexenes have been investigated. 1,4-Elimination is heavily favored over 1,2-elimination when strong bases such as hydroxide and amide are used. The 1,2-pathway becomes more competitive when weaker bases such as methoxide are employed, and the mechanism shifts from E1 cB to E2.

Original languageEnglish (US)
Pages (from-to)4077-4080
Number of pages4
JournalTetrahedron Letters
Issue number33
StatePublished - Aug 12 1991

Bibliographical note

Funding Information:
.Acknowl edgement: Support from the National Science Foundation (CHE-8907 198)a nd the donors of the PetroleumR esearchF oundationa rc gratefullya cknowledged.


  • 3-methoxycyclohexene
  • elimination
  • flowing afterglow
  • gas-phase
  • regiochemistry


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