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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 23
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Original Articles

Selective Apical Bromination of Diamantane and Conversion to the Dihydroxy and Dicarboxylic Acid Derivatives

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Pages 3509-3514 | Received 09 May 2006, Published online: 24 Nov 2006
 

Abstract

New conditions have been found that provide for the selective bromination of diamantane at the 4,9‐positions. Subsequent hydrolysis and Koch–Haaf reaction gave the 4,9‐dihydroxy‐ and 4,9‐dicarboxylic acid derivatives, respectively.

Acknowledgments

The authors thank the Office of Naval Research for generous support of this project. The authors also thank Andrew P. Chafin (NAWCWD) and Dr. Robert M. Carlson (Chevron, Richmond, CA) for comments and suggestions regarding this manuscript.

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