Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide

Lee M. Bishop, Michael Winkler, Kendall N. Houk, Robert G. Bergman, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A study was conducted to perform mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-Quinone methide (QM). The study focused on mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-Quinone methide, as led to the formation of chromenes. Vinyl o-QM was prepared through oxidation of phenol 3, while the E configuration of the exo-alkylidene bond was established by detailed nuclear magnetic resonance (NMR) studies and X-ray crystallography. The structure of the dimer was also confirmed by X-ray crystallography. Kinetic investigation of the uncatalyzed cyclization of Vinyl o-QM and chromene revealed the sensitivity of the rate of the reaction to light, oxygen, and adventitious acid, studying the reactivity of o-QM.

Original languageEnglish (US)
Pages (from-to)5405-5408
Number of pages4
JournalChemistry - A European Journal
Volume14
Issue number18
DOIs
StatePublished - Jun 20 2008

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Cyclization
X ray crystallography
Acids
Benzopyrans
Dimers
Phenols
Nuclear magnetic resonance
Oxidation
Phenol
Kinetics
Oxygen
quinone methide

Keywords

  • Activation parameters
  • Alkenes
  • Density functional calculations
  • Dimerization
  • Isomerization

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide. / Bishop, Lee M.; Winkler, Michael; Houk, Kendall N.; Bergman, Robert G.; Trauner, Dirk.

In: Chemistry - A European Journal, Vol. 14, No. 18, 20.06.2008, p. 5405-5408.

Research output: Contribution to journalArticle

Bishop, Lee M. ; Winkler, Michael ; Houk, Kendall N. ; Bergman, Robert G. ; Trauner, Dirk. / Mechanistic investigations of the acid-catalyzed cyclization of a vinyl ortho-quinone methide. In: Chemistry - A European Journal. 2008 ; Vol. 14, No. 18. pp. 5405-5408.
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