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syn ‐ and anti ‐Bishomoanthraquinone
Author(s) -
Vogel Emanuel,
Böhm Stefan,
Hedwig Achim,
Hergarten Bernd O.,
Lex Johann,
Uschmann Joachim,
Gleiter Rolf
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198610001
Subject(s) - solvolysis , steric effects , chemistry , halogenation , stereoselectivity , anthraquinone , derivative (finance) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , hydrolysis , financial economics , economics
The remarkable regio‐ and stereoselectivity of the bromination of syn ‐bismethano[14]annulene 1 can be explained in terms of pronounced π/σ interactions in 1 . The product is almost exclusively (90%) the 7,14‐dibromo derivative 2 , which can be converted via solvolysis and oxidation into the syn ‐bishomoanthraquinone 3 . With regards to its quinonoid properties, this potential building block for “bishomoanthraquinone dyes” compares with anthraquinone rather than with p ‐benzoquinone. For steric reasons, in the case of the anti ‐isomer of 3 the quinonoid character diminishes further.