Phenanthrenes 1,2,3,4-tetrahydro— from

Phenanthrenes are formed by the reaction of 2-iodobiaryls with alkynes. The 1,2,3,4-tetrahydro derivatives are similarly obtained from the corresponding reaction with 2-iodo-1 -arylcyclohexenes. ... 

Heterocyclic Synthesis. - The reactions of phosphorus ylides with phenan-threne-9,10-quinone (113) have been used to prepare phenanthrene [9,10-x]-fused compounds with four, five, and six membered heterocyclic rings. (E)-4-carbethoxymethylene-l,2,3,4-tetrahydro-2-quinolones 114 have been obtained from the stereoselective reaction of 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones and ethyl(triphenylphosphoranylidene)acetate. A -trifluoroacetylanilines 115 react with Ph3P=C02Et producing enamine derivatives 116 as a mixture of (E)- and (Z)-isomers. Enamines 116 are useful precursors for the synthesis of indoles and quinolones. 

This material is synthesized from 4-(3,5-dinitrobenzamido)-tetrahydro-phenanthrene which is also covalently bonded to silica particles 5 pm in diameter. It is used to separate the underivatized isomers of drugs such as Ibuprofen and Naproxen. It is a fairly stable phase and is available in both enantiomeric forms allowing elution order reversal if so desired. 

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