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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 6
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Original Articles

Synthesis of 9,10-Phenanthrenequinones by Photocyclization of Derivatives of Benzoins: Scope and Limitation of the Methodology

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Pages 1051-1063 | Received 01 Sep 1997, Published online: 20 Aug 2006
 

Abstract

Symmetric 9,10-phenanthrenequinones with methyl, methoxy, and chloro substituents at the 3 and 6 positions have been synthesized by photocyclization of 4,5-bis-(aryl)-2-phenyl-1,3,2-dioxaboroles and 2,3-diaryldioxenes followed by oxidative hydrolysis.

Notes

The yield of benzoin was 83%, 4,4′-dimethoxibenzoin was 75%, 4,4′-dichlorobenzoin was 67%, 4,4′-dimethylbenzoin was 61%, and 4-methoxy benzoin was 25%.

This signal disappeared upon addition of D2O.

No ketal was obtained.

The same melting point and infrared spectra.

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