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Silyl‐Substituted Tetrathia[7]helicenes: Synthesis, X‐ray Characterization and Reactivity
Author(s) -
Bossi Alberto,
Maiorana Stefano,
Graiff Claudia,
Tiripicchio Antonio,
Licandro Emanuela
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700494
Subject(s) - chemistry , helicene , benzothiophene , silylation , electrophilic substitution , dihedral angle , reactivity (psychology) , alkene , thiophene , electrophile , x ray , stereochemistry , medicinal chemistry , organic chemistry , molecule , catalysis , medicine , hydrogen bond , physics , alternative medicine , pathology , quantum mechanics
Abstract We describe the synthesis of trialkylsilyl‐substituted trans ‐1,2‐bis(thieno[3,2‐ e ]benzothiophene‐2‐yl)ethenes as suitable soluble precursors for the preparation of the corresponding silylated tetrathia[7]helicenes, which, in turn, can be desilylated or transformed into dihalogen‐substituted derivatives through electrophilic substitution of silyl substituents. X‐ray structural studies showed that the presence of the two triisopropylsilyl groups on the terminal thiophene rings accounts for the high solubility of the alkene and for the very large dihedral angle in the helicene. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)