Phenanthrene-9,10-imines

Studies of the photodecomposition of phenanthrene 9,10-imine, 1-benzyloxypyrid-2-one, and methyl phenobarbital have also been reported, and the effect of an external field on photoinduced substitution in 4-methylquinoline-2-carbonitrile has been described. ... 

S1097>. Reactions of phenanthrene-9,10-imine (20 R = H) with nucleophiles like NaN3 or RSCN under phase-transfer conditions gives compounds (62) and (63) respectively <84JHC1597>, while (20 R = C1) undergoes an unusual transformation to 9,10-phenanthroquinone dialkyl monoacetal (64) in a silver-promoted reaction (Scheme 23) <84JHC1593>. 

Y. Utah, Y. Sasson, I. Shahak, S. Tsaroom, and J. Blum, A new aziridine synthesis from 2-azido alcohols and tertiary phosphines. Preparation of phenanthrene 9,10-imine, J. Org. 

The reaction has been applied to nonheterocyclic aromatic compounds Benzene, naphthalene, and phenanthrene have been alkylated with alkyllithium reagents, though the usual reaction with these reagents is 12-20, and Grignard reagents have been used to alkylate naphthalene. The addition-elimination mechanism apparently applies in these cases too. A protected form of benzaldehyde (protected as the benzyl imine) has been similarly alkylated at the ortho position with butyl-lithium. ... 

Lithiation of imines and acetylene Imines and acetylenes can be lithiated directly by reaction with metallic lithium in THF at 10° with phenanthrene as the hydrogen acceptor (it is converted into 1,2,3,4,5,6,7,8-octahydrophenanthrene). 

This method was used to convert phenanthrene-9,10-oxide into the 9,10-imine in 72% yield. This imine is thermally stable at temperatures up to 190°. 

Phenanthrene synthesis. A new phenanthrene synthesis employs the nickel(O)-catalyzed condensation of the imine 1 with 2 to give, after hydrolysis, the aldehyde 3. This product was converted in several steps to the phenanthrene 4, which is a key... 

In an analogous system, it was found that a phenanthrene o-quinodimethane, generated by a reductive process, acted as a diene in [4 + 2] cycloadditions with two neutral imines to give pentacyclic adducts, although yields were rather low [Eq. (17)].68... 

Arene imines. The N-acetyl imine of the so-called K region of phenanthrene has been prepared (equation I). ... 

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