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The chemistry of polycyclic arene imine. VI. 1‐[ N,N ‐di‐(2‐propenyl)‐9‐phenanthreneamine‐10‐yl]‐1a,9b‐dihydrophenanthro[9,10‐ b ]azirine an unusual allylation product of phenanthrene 9,10‐imine
Author(s) -
Weitzberg Moshe,
Aizenshtat Zeev,
Blum Jochanan
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220352
Subject(s) - chemistry , imine , phenanthrene , azirine , medicinal chemistry , iminium , deprotonation , allyl bromide , propenyl , stereochemistry , organic chemistry , catalysis , ring (chemistry) , ion
Phenanthrene 9,10‐imine (1) was shown to react with allyl bromide and 50% aqueous sodium hydroxide under phase transfer catalysis conditions to give the title compound 3 as the only product. The starting imine 1 is assumed to undergo initially bis alkylation to form an N,N ‐di‐(2‐propenyl)phenanthrene 9,10‐iminium salt (4) which, in turn, is attacked by a deprotonated phenanthrene imine anion (5). The structure of 3 has been determined by a single crystal X‐ray diffraction analysis.