942935-18-4Relevant academic research and scientific papers
On the functionalization of [2.2](1,4)phenanthrenoparacyclophane
Hopf, Henning,Hucker, Joachim,Ernst, Ludger
, p. 1891 - 1904 (2008/02/06)
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 bronudes (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, 2007.
