Acid-Catalyzed Ring-Opening Isomerizations of Cyclopropenes

Lien H. Phun; Joel Aponte-Guzman; Stefan France

doi:10.1055/s-0032-1317169

Synlett, Table of Contents

Synlett 2012; 23(19): 2723-2728
DOI: 10.1055/s-0032-1317169

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Acid-Catalyzed Ring-Opening Isomerizations of Cyclopropenes

Lien H. Phun

School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA Fax: +1(404)8947452 Email: stefan.france@chemistry.gatech.edu

,

Joel Aponte-Guzman

School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA Fax: +1(404)8947452 Email: stefan.france@chemistry.gatech.edu

,

Stefan France*

School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA Fax: +1(404)8947452 Email: stefan.france@chemistry.gatech.edu

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Abstract

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Abstract

Acid-catalyzed cyclopropene cycloisomerizations are discussed as a means to generate ring systems. Herein, the recent results obtained in our group are contrasted with previous examples in the literature. Particular emphasis is placed on the mode of activation which, for our case, results in a different ring-opening mechanism than previously observed. The potential of the method as a tool for organic chemists is demonstrated by the synthesis of a host of benzo-fused heteroaromatic and heterobiaryl products.

Key words

cyclopropenes - annulations - Friedel–Crafts reaction - fused ring systems - arenes

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References

References and Notes
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