The chemistry of polycyclic arene imines. III. N-alkylation of phenanthrene 9,10-imineN-alkylation of phenanthrene 9,10-imine |
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Authors: | Sarah Shtelzer Moshe Weitzberg Juliette Jeries Tuvia Sheradsky Zeev Aizenshtat Jochanan Blum |
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Institution: | Department of Organic Chemistry, The Hebrew University, Jerusalem 91904, Israel |
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Abstract: | Phenanthrene 9,10-imine ( 1 ) was shown to undergo N-alkylation without aziridine ring cleavage by (a) metallation with sodium methylsulfinylmethide followed by addition of an alkyl halide at ?20° (b) reaction of 1 , sodium hydride and the halide in dimethylformamide at 40° (c) treatment of a dichloromethane solution of 1 , the halide and triethylbenzylammonium chloride with aqueous sodium hydroxide under phase transfer conditions. The syntheses of N-isopropyl-, N-butyl-, N-pentyl-, N-allyl- and N-benzylphenanthrene 9,10-imine ( 2–6 ) are described. |
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