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

doi:10.1002/chem.200800662

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	5405-5408
Number of pages	4
Journal	Chemistry - A European Journal
Volume	14
Issue number	18
DOIs	https://doi.org/10.1002/chem.200800662
State	Published - Jun 20 2008

Keywords

Activation parameters
Alkenes
Density functional calculations
Dimerization
Isomerization

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.200800662

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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.",

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AU - Bishop, Lee M.

AU - Winkler, Michael

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AU - Bergman, Robert G.

AU - Trauner, Dirk

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KW - Alkenes

KW - Density functional calculations

KW - Dimerization

KW - Isomerization

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

Abstract

Keywords

ASJC Scopus subject areas

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