Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 19
156
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Preparation of Substituted Dihydrofluorenones by Photoisomerization of Benzotropolone Derivatives

, , , &
Pages 2852-2858 | Received 07 May 2010, Published online: 29 Jun 2011
 

Abstract

The photoisomerization of the Diels–Alder adduct formed between tetramethylpurpurogallin and maleic anhydride is described. The process is highly stereoselective, involves the β,γ-unsaturated ketone chromophore present in the adduct, proceeds through the formation of allyl and aroyl radical intermediates, and leads to a novel substituted dihydrofluorenone in good yields.

ACKNOWLEDGMENTS

Financial support from the Agencia Nacional de Investigación e Innovación, the Comision Sectorial de Investigación Científica, the National Science Foundation, and the Royal Society of Chemistry is acknowledged. We also thank Alexander Khrizman for technical support.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.