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Macrocyclic pyridinophanetetraene
Author(s) -
Thilgen Carlo,
Vögtle Fritz
Publication year - 1990
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19901231228
Subject(s) - chemistry , pyridine , chloride , copper , stereochemistry , medicinal chemistry , double bond , coupling reaction , polymer chemistry , organic chemistry , catalysis
The new pyridinophanetetraene 4 has been prepared in a two‐step synthesis by a modified Kharash coupling reaction of 2,6‐bis[3‐lithio‐( E )‐styryl]pyridine with copper(II) chloride. Starting from isomerically pure 2,6‐bis[3‐bromo‐( E )‐styryl]pyridine (3), the cyclization reaction takes place without rearrangement of the stilbazole double bonds. The electronic spectrum of 4 shows characteristic differences when compared to that of its open‐chain analogue 2,6‐bis[( E )‐styryl]pyridine ( 7 ).
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