The Journal of organic chemistry

A Novel Strategy for the Synthesis of Oxygenated Phenanthrenes Involving a Combination of Ullmann and McMurry Reactions

AE Gies, M Pfeffer

Index: Gies, Anne-Elisabeth; Pfeffer, Michel Journal of Organic Chemistry, 1999 , vol. 64, # 10 p. 3650 - 3654

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Citation Number: 30

Abstract

A general synthetic procedure for the preparation of polyoxygenated phenanthrenes from substituted derivatives of benzaldehyde is described. The key compound is a 6, 6'-biphenyl- 1, 1'-dicarboxaldehyde intermediate formed through an ambient temperature Ullmann coupling. The subsequent McMurry condensation gave rise to the phenanthrene in 45-57% yields.