Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

The Benzyne Story

Curt Wentrup A
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia. Email: wentrup@uq.edu.au

Australian Journal of Chemistry 63(7) 979-986 https://doi.org/10.1071/CH10179
Submitted: 2 May 2010  Accepted: 3 June 2010   Published: 15 July 2010

Abstract

The history of o-benzyne from its early beginnings as an unobservable reactive intermediate until its present status as a very well characterized but still theoretically challenging molecule with important applications in synthesis is reviewed. The m- and p-benzynes, tridehydrobenzenes, and benzdiynes are also known, and p-benzyne is a key intermediate in the action of a potent class of ene-diyne anti-tumour compounds.


References


[1]   (a) W. E. Bachmann, H. T. Clarke, J. Am. Chem. Soc. 1927, 49,  2089.
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
         
         
        | Crossref |  GoogleScholarGoogle Scholar |  Another 18 computational papers on benzynes from 1969 to 1984 are cited herein.

[19]   H. Winkler, W. Sander, Aust. J. Chem. 2010, 63,  1013.
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  open url image1