Silyl‐Substituted Tetrathia[7]helicenes: Synthesis, X‐ray Characterization and Reactivity | Zendy

Bossi Alberto | Zendy; Maiorana Stefano | Zendy; Graiff Claudia | Zendy; Tiripicchio Antonio | Zendy; Licandro Emanuela | Zendy

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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

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)

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