Synthesis of Functionalized Tetracyanocyclopentadienides from Tetracyanothiophene and Sulfones

Tetracyanothiophene and tetracyano-1,4-dithiin react with a leaving group substituted carbon nucleophile such as ethyl benzenesulfonylacetate to afford substituted tetracyanocyclopentadienyl sodium derivatives in moderate to high yields through a putative condensation and desulfurization pathway. Su...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 21; pp. 10978 - 10985
Main Authors Sakai, Takeo, Seo, Shohei, Matsuoka, Junpei, Mori, Yuji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Molecular Structure
Nitriles - chemical synthesis
Nitriles - chemistry
Physical Sciences
Science & Technology
Sulfones - chemistry
Thiophenes - chemistry
ION
ANION
TETRACYANO-1,4-DITHIIN
COMPLEXES
THIACYANOCARBONS
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Summary:Tetracyanothiophene and tetracyano-1,4-dithiin react with a leaving group substituted carbon nucleophile such as ethyl benzenesulfonylacetate to afford substituted tetracyanocyclopentadienyl sodium derivatives in moderate to high yields through a putative condensation and desulfurization pathway. Subsequent functional-group transformation reactions on the Cp anion ring provided various C5R(CN)4 – derivatives.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401946j