Premium
Highly Twisted Arenes by Scholl Cyclizations with Unexpected Regioselectivity
Author(s) -
Pradhan Anirban,
Dechambenoit Pierre,
Bock Harald,
Durola Fabien
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105105
Subject(s) - regioselectivity , helicene , steric effects , twist , chemistry , stereochemistry , organic chemistry , mathematics , molecule , catalysis , geometry
Let's twist! The Scholl reaction with quinquephenyl derivatives has been shown to have an unexpectedly strong preference for forming twisted, helicene aromatic polycycles, instead of their flat counterparts. This tendency is so strong that it will overcome even severe steric hindrance, and the procedure can be used in the efficient synthesis of hexa‐ tert ‐butylhexabenzotriphenylene from a simple biaryl starting material (see scheme).