Premium
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.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom