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On the Functionalization of [2.2](1,4)Phenanthrenoparacyclophane
Author(s) -
Hopf Henning,
Hucker Joachim,
Ernst Ludger
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601129
Subject(s) - chemistry , formylation , halogenation , phenazine , surface modification , electrophile , acylation , metalation , electrophilic substitution , friedel–crafts reaction , organic chemistry , regioselectivity , phenols , electrophilic aromatic substitution , polyene , combinatorial chemistry , catalysis
Two routes for preparing functionalized [2.2](1,4)phenanthrenoparacyclophanes are described: either the parent system 2 is subjected to electrophilic substitution (bromination, Friedel–Crafts acylation, Rieche formylation: preparation of 5 , 6 , 7 , 11 and 12 ) or the desired substituents are incorporated in the early stages of the synthesis by the preparation of the corresponding functionalized styryl paracyclophanes and their photocyclization to the respective phenanthrenocyclophanes. By these specific routes various bromides ( 22a , b ), ethers ( 28a – c ) and phenols ( 29a , b ) were synthesized. The latter derivatives, on oxidation, furnish para ‐ ( 31 ) and ortho ‐quinonophanes ( 30 , 32 , 33 ), useful substrates for the preparation of cyclophanes containing phenazine subunits ( 36 ). The stilbene → phenanthrene photocyclization can also be employed for the preparation of benzothiophenophanes, e.g. 43 and 44 , from the respective precursors. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)