Issue 33, 2005
From the journal:

Chemical Communications

Ketonization of the remarkably strongly acidic elongated enol generated by flash photolytic decarboxylation of p-benzoylphenylacetic acid in aqueous solution†

Yvonne Chiang,a   A. Jerry Kresge,*a   Ikenna Onyido,a   John P. Richard,b   Peter Wanc  and  Musheng Xuc  

* Corresponding authors

a Department of Chemistry, University of Toronto, Toronto, Ontario, Canada
E-mail: akresge@chem.utoronto.ca
Fax: +1 (416)978-7259
Tel: +1 (416)978-7259

b Department of Chemistry, University at Buffalo, SUNY, Buffalo, New York 14260-3000, USA

c Department of Chemistry, Box 3065, University of Victoria, Victoria, British Columbia, Canada

Abstract

Photodecarboxylation of p-benzoylphenylacetic acid in aqueous solution produces the elongated enol 5, whose strength as an oxygen acid (pQEa = 7.67) makes it more acidic than simple enol analogs by several orders of magnitude.

Graphical abstract: Ketonization of the remarkably strongly acidic elongated enol generated by flash photolytic decarboxylation of p-benzoylphenylacetic acid in aqueous solution

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Article information

DOI
https://doi.org/10.1039/B506706E
Article type
Communication
Submitted
11 May 2005
Accepted
29 Jun 2005
First published
27 Jul 2005

Chem. Commun., 2005, 4231-4233

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Ketonization of the remarkably strongly acidic elongated enol generated by flash photolytic decarboxylation of p-benzoylphenylacetic acid in aqueous solution

Y. Chiang, A. J. Kresge, I. Onyido, J. P. Richard, P. Wan and M. Xu, Chem. Commun., 2005, 4231 DOI: 10.1039/B506706E

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