Regioselectivity in gas-phase elimination reactions: 1,2 vs 1,4 and allenic ion vs dienide formation

John J. Rabasco, Steven R Kass

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10 Scopus citations

Abstract

Gas-phase elimination reactions of deuterium labeled 1-allyl-1-methoxy-6,6-dimethyl-2-cyclohexene (1), 1-methoxy-4,4-dimethyl- 1-vinyl-2-cyclohexene (2) and 3-methoxy-3-methyl-1-butene (3) have been investigated. 1,2-Elimination is the favored pathway when 1 reacts with hydroxide (3.5:1) and methoxide (2.6:1), but 1,4-elimination is preferred with fluoride by 2:1. Abstraction of a vinyl proton in the elimination reactions of 2 and 3 is dominant when amide and/or dimethylamide are used, whereas the loss of an alkyl proton is heavily favored with hydroxide.

Original languageEnglish (US)
Pages (from-to)765-768
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number5
DOIs
StatePublished - Jan 29 1993

Keywords

  • eliminations
  • flowing afterglow
  • gas-phase
  • methyl ethers
  • regiochemistry

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