Synlett 2012; 23(19): 2723-2728
DOI: 10.1055/s-0032-1317169
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© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 09 July 2012

Accepted after revision: 06 August 2012

Publication Date:
31 October 2012 (online)

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.

 
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