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Construction of a Highly Distorted Benzene Ring in a Double Helicene
Author(s) -
Hashimoto Sigma,
Nakatsuka Soichiro,
Nakamura Masaharu,
Hatakeyama Takuji
Publication year - 2014
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.201408390
Subject(s) - helicene , intramolecular force , ring (chemistry) , benzene , molecule , tandem , aromaticity , chemistry , crystallography , distortion (music) , ligand (biochemistry) , materials science , stereochemistry , organic chemistry , optoelectronics , amplifier , biochemistry , receptor , cmos , composite material
A P‐fused double helicene consisting of a highly distorted benzene ring, with a bending angle of 23°, has been synthesized by a tandem intramolecular phospha‐Friedel–Crafts reaction. Despite the distortion and reduced aromaticity, the double helicene shows thermal and chemical stability. These are important features that make these compounds attractive for applications as a new C 2 ‐symmetric bisphosphine ligand. The simple strategy proposed in this work can be used to prepare a diverse range of distorted molecules.