A 1,3-carbonyl shift in the platinum-catalyzed aromatization of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes

Rupsha Chaudhuri; Arindam Das; Hsin-Yi Liao; Rai-Shung Liu

doi:10.1039/c002660c

A 1,3-carbonyl shift in the platinum-catalyzed aromatization of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes

Chem Commun (Camb). 2010 Jul 7;46(25):4601-3. doi: 10.1039/c002660c. Epub 2010 May 18.

Authors

Rupsha Chaudhuri¹, Arindam Das, Hsin-Yi Liao, Rai-Shung Liu

Affiliation

¹ Department of Chemistry National Tsing Hua University, Hsinchu, 30013, Taiwan, ROC.

PMID: 20485774
DOI: 10.1039/c002660c

Abstract

A platinum-catalyzed reaction involving new aromatization/1,3-carbonyl shift cascade of 2-epoxy-1-(methoxyalk-2-ynyl)benzenes is reported. This skeletal rearrangement is mechanistically significant because it involves a remarkable 1,3-carbonyl shift to complete the aromatization and to regenerate the catalyst.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzene Derivatives / chemical synthesis*
Benzene Derivatives / chemistry*
Catalysis
Molecular Structure
Organometallic Compounds / chemistry*
Platinum / chemistry*
Stereoisomerism

Substances

Benzene Derivatives
Organometallic Compounds
Platinum