Degenerate thermal isomerizations of bicyclo[3.1.1]hept-2-ene: Strategy and analysis

John E. Baldwin, Bruce S. Hudson

Research output: Contribution to journalArticle

Abstract

Bicyclo[3.1.1]hept-2-ene was first prepared and well identified in 1972. In 1974, the degenerate thermal isomerization involving 1-d- and 3-d-bicyclo[3.1.1]hept-2-ene was approached successfully, as one of the two deuterium-labeled structures was selected, heated, and equilibrated. There has been no further study of this degenerate isomerization. Here, a detailed outline of reaction trajectories for d2-labeled bicyclo[3.1.1]hept-2-enes is given that will establish the four independent kinetic parameters needed for 20 linking paths between six d2-species. The use of racemates, eliminating chiral separations and dissections, provides degenerate isomerization paths providing this method with general utility.

Original languageEnglish (US)
Pages (from-to)213-217
Number of pages5
JournalJournal of Physical Organic Chemistry
Volume27
Issue number3
DOIs
StatePublished - Mar 1 2014

Keywords

  • C deuterium shifts
  • bicyclo[3.1.1]hept-2-ene
  • deuterium labels
  • epimers
  • thermal [1,3] carbon shifts

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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