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Palladium‐Catalyzed Sixfold Alkenylation of Hexabromobenzene: An Interesting Case of Self‐Organization
Author(s) -
Prinz Peter,
Lansky Annegret,
Knieriem Burkhard,
de Meijere Armin,
Haumann Thomas,
Boese Roland,
Noltemeyer Matthias
Publication year - 1997
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.199712891
Subject(s) - benzene , palladium , ring (chemistry) , catalysis , alkyl , medicinal chemistry , chemistry , coupling (piping) , stereochemistry , materials science , organic chemistry , composite material
Bowl‐shaped hexakis(3,3‐dimethyl‐1‐butenyl)benzene ( 1 , see space‐filling model on the right) was obtained from the Pd‐catalyzed coupling of hexabromobenzene with 2‐(3,3‐dimethyl‐1‐butenyl)‐1,3,2‐benzodioxaborole. All six alkenyl groups are directed to one side of the benzene ring. Catalytic hydrogenation of 1 provides the corresponding hexakisalkylbenzene, which crystallizes in regular stacks; here the alkyl group are alternatingly above and below the ring.