Premium
Tetrakis(alkylthio)thieno[3,4‐ c ]thiophene: Synthesis, stability, and reactivity
Author(s) -
Yoneda Shigeo,
Tsubouchi Kenji Ozaki, Akira,
Kojima Hideo,
Yanagi Kazunori
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250238
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , cycloaddition , reactivity (psychology) , thiophene , medicinal chemistry , chemical stability , organic chemistry , catalysis , medicine , alternative medicine , pathology
The synthesis of tetrakis(alkylthio)thieno[3,4‐ c ]thiophenes la‐e by the dimerization reaction of bis(alkylthio)cyclopropenethiones is described. The remarkable thermodynamic and kinetic stability suggests the significant electron‐accepting conjugation of the alkylthio substituents to the carbanionic 1, 3, 4, and 6 carbons in the framework. The isopropylthio‐ and ethylthio‐substituted thienothiophenes 1d and 1e undergo cycloaddition reactions with dienophiles such as N ‐phenylmaleimide and dimethyl acetylenedicarboxylate to give the cycloadducts in moderate yields.