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Electron‐Accepting Dithiarubicene (Emeraldicene) and Derivatives Prepared by Unprecedented Nucleophilic Hydrogen Substitution by Alkyllithium Reagents
Author(s) -
Mohebbi Ali Reza,
Wudl Fred
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201002608
Subject(s) - reagent , chemistry , alkylation , nucleophile , nucleophilic substitution , solvent , hydride , molecule , combinatorial chemistry , nucleophilic aromatic substitution , stack (abstract data type) , substitution reaction , hydrogen , catalysis , medicinal chemistry , organic chemistry , computer science , programming language
By understanding the role of DMF as a hydride source via a Pd‐catalyzed reaction and switching to CH 3 CN solvent, an efficient route for the synthesis of emeraldicene and some new substituted derivatives is reported with potential application in organic electronics. Additionally, the nucleophilic alkylation of emeraldicene 4 a with alkyllithium reagents provides monosubstituted compounds 7 a and 7 b , the latter crystallizing in columnar stacks, with π–π overlap between adjacent molecules in the stack.